Skip to main content
SpringerLink
Log in

Phomactin A

  • Chapter
  • First Online:
Total Synthesis of Natural Products

  • 3409 Accesses

Abstract

Marine organisms have provided a highly diversified natural product structures with a wide range of biological properties [1], leading to intense isolation, synthesis, and medicinal chemistry efforts. In particular, marine fungi have received much recent interest due to the radically different environment from which they have adapted, relative to their terrestrial counterparts.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. For reviews, see: (a) Molinski TF, Dalisay DS, Lievens SL, Saludes JP (2009) Nat Rev Drug Dis 8:69; (b) Blunt JW, Copp BR, Munro MGH, Northcotec PT, Prinsep MR (2003) Nat Prod Rep 20:1; (c) Faulkner DJ (2000) Nat Prod Rep 17:1; (d) Simmons TL, Andrianasolo E, McPhail K, Flatt P, Gerwick WH (2005) Mol Cancer Ther 4:333

    Google Scholar 

  2. Sugano M, Sato A, Iijima Y, Oshima T, Furuya K, Kuwano H, Hata T, Hanzawa H (1991) J Am Chem Soc 113:5463

    Article  CAS  Google Scholar 

  3. Sugano M, Sato A, Iijima Y, Oshima T, Furuya K, Haruyama H, Yoda K, Hata T (1994) J Org Chem 59:564

    Article  CAS  Google Scholar 

  4. Sugano M, Sato A, Iijima Y, Oshima T, Furuya K, Kuwano H, Hata T (1995) J Antibiot 48:1188

    Article  CAS  Google Scholar 

  5. Koyama K, Ishino M, Takatori K, Sugita T, Kinoshita K, Takahashi K (2004) Tetrahedron Lett 45:6947

    Article  CAS  Google Scholar 

  6. Chu M, Truumees I, Gunnarsson I, Bishop WR, Kreutner W, Horan AC, Patel MG, Gullo VP, Puar MS (1993) J Antibiot 46:554

    Article  CAS  Google Scholar 

  7. Chu M, Patel MG, Gullo VP, Truumees I, Puar MS, McPhail AT (1992) J Org Chem 57:5817

    Article  CAS  Google Scholar 

  8. Cheing JWC, Goldring WPD, Pattenden G (2003) Chem Commun 2788

    Google Scholar 

  9. Tokiwano T, Fukushi E, Endo T, Oikawa H (2004) Chem Commun 1324

    Google Scholar 

  10. Mahato SB, Pal BC, Kawasaki T, Miyahara K, Tanaka O, Yamasaki K (1979) J Am Chem Soc 101:4720

    Article  CAS  Google Scholar 

  11. Stafforinif DM, McIntyre TM, Zimmerman GA, Prescott SM (2003) Crit Rev Clin Lab Sci 40:643

    Article  Google Scholar 

  12. Sugano M, Sato A, Saito K, Takaishi S, Matsushita Y, Iijima Y (1996) J Med Chem 39:5281

    Article  CAS  Google Scholar 

  13. Braquet P, Touqui L, Shen TY, Varaftig BB (1987) Pharm Rev 39:97–145

    CAS  Google Scholar 

  14. Nagase T, Ishii S, Kume K, Uozumi N, Izumi T, Ouchi Y, Shimizu T (1999) J Clin Invest 104:1071

    Article  CAS  Google Scholar 

  15. Zhu X, Lambertino AT, Houghton TJ, McGilvra JD, Xu C, Rawal VH, Leff AR (2003) Life Sci 73:3005

    Article  CAS  Google Scholar 

  16. For an excellent review on synthetic efforts toward phomactins, see: Goldring WPD, Pattenden G (2006) Acc Chem Res 39:354

    Google Scholar 

  17. Also see: Cole KP, Hsung RP (2003) ChemTracts 16:811

    Google Scholar 

  18. For approaches, see: (a) Foote KM, Hayes CJ, Pattenden G (1996) Tetrahedron Lett 37:275; (b) Chen D, Wang J, Totah NI (1999) J Org Chem 64:1776; (c) Seth PP, Totah NI (1999) J Org Chem 64:8750; (d) Seth PP, Totah NI (2000) Org Lett 2:2507; (e) Kallan NC, Halcomb RL (2000) Org Lett 2:2687; (f) Chemler SR, Danishefsky SJ (2000) Org Lett 2:2695; (g) Seth PP, Chen D, Wang J, Gao X, Totah NI (2000) Org Lett 56:10185; (h) Foote K, John M, Pattenden G (2001) Synlett 365; (i) Mi B, Maleczka R (2001) Org Lett 3:1491; (j) Chemler SR, Iserloh U, Danishefsky SJ (2001) Org Lett 3:2949; (k) Houghton T, Choi S, Rawal VH (2001) Org Lett 3:3615; (l) Mohr PJ, Halcomb RL (2002) Org Lett 4:2413; (m) DiBlasi CM, Hamblett CL, Leighton JL (2002) Abstracts of Papers, 224th ACS-National Meeting, Boston, MA, 2002; ORGN-364; (n) DiBlasi CM (2003) Ph.D. Dissertation. Thesis Advisor: Professor James L. Leighton, Columbia University; (o) Balnaves AS, McGowan G, Shapland PDP, Thomas EJ (2003) Tetrahedron Lett 44:2713; (p) Cheing JWC, Goldring WPD, Pattenden G (2003) Chem Commun 2788; (q) Ryu K, Cho Y-S, Jung S-I, Cho C-G (2006) Org Lett 8:3343; (r) Huang J, Wang H, Wu C, Wulff WD (2007) Org Lett 9:2799; (s) Seth PP, Chen D, Wang J, Gao X, Totah NI (2007) Tetrahedron Lett 48:4605; (t) Peng W, Lee C-S (2008) Synlett 142; Sugano M, Sato A, Iijima Y, Furuya K, Hata T, Kuwano H (1995) J Antibiot 48:1188; (u) Ciesielski J, Canterbury DP, Frontier AJ (2009) Org Lett 11:4374; (v) Shapland PDP, Thomas EJ (2009) Tetrahedron 65:4201; (w) Blackburn TJ, Helliwell M, Kilner M, Lee ATL, Thomas EJ (2009) Tetrahedron Lett 50:3550; (x) Schwartz KD, White JD (2011) Org Lett 13:248; (y) Huang S, Du G, Lee C-S (2011) J Org Chem 76:6534

    Google Scholar 

  19. For total synthesis of (+)-phomactin D, see: Miyaoka H, Saka Y, Miura S, Yamada Y (1996) Tetrahedron Lett 37:7107

    Google Scholar 

  20. For total synthesis of (±)-phomactin B2, see: Huang J, Wu C, Wulff WD (2007) J Am Chem Soc 129:13366

    Google Scholar 

  21. For total synthesis of (±)-phomactin A, see: (a) Goldring WPD, Pattenden G (2002) Chem Commun 1736; For detailed full papers, see: (b) Diaper CM, Goldring WPD, Pattenden G (2003) Org Biomol Chem 1:3949; (c) Foote KM, Hayes CJ, John MP, Pattenden G (2003) Org Biomol Chem 1:3917

    Google Scholar 

  22. For total synthesis of (+)-phomactin A, see: Mohr PJ, Halcomb RL (2003) J Am Chem Soc 125:1712

    Google Scholar 

  23. For total synthesis of (±)-phomactin G, see: Goldring WPD, Pattenden G (2004) Org Biomol Chem 2:466

    Google Scholar 

  24. Harrity JPA, Provoost O (2005) Org Biomol Chem 3:1349

    Article  CAS  Google Scholar 

  25. Hsung RP, Kurdyumov AV, Sydorenko N (2005) Eur J Org Chem 1:23

    Article  Google Scholar 

  26. Hsung RP, Wei L-L, Sklenicka HM, Shen HC, McLaughlin MJ, Zehnder LR (2001) Trends Heterocycl Chem 7:1–24

    CAS  Google Scholar 

  27. Hsung RP, Cole KP (2004) In: Harmata M (ed) Strategies and tactics in organic synthesis, vol 4. Elsevier Science, Pergamon, Oxford, UK, p 41

    Chapter  Google Scholar 

  28. Buchanan GS, Feltenberger JB, Hsung RP (2010) Curr Org Syn 7:363

    Article  CAS  Google Scholar 

  29. Hsung RP, Shen HC, Douglas CJ, Morgan CD, Degen SJ, Yao LJ (1999) J Org Chem 64:690

    Article  CAS  Google Scholar 

  30. Hsung RP, Wei L-L, Sklenicka HM, Douglas CJ, McLaughlin MJ, Mulder JA, Yao L (1999) Org Lett 1:509

    Article  CAS  Google Scholar 

  31. Shen HC, Wang J, Cole KP, McLaughlin MJ, Morgan CD, Douglas CJ, Hsung RP, Coverdale HA, Gerasyuto AI, Hahn JM, Liu J, Wei L-L, Sklenicka HM, Zehnder LR, Zificsak CA (2003) J Org Chem 68:1729

    Article  CAS  Google Scholar 

  32. Kurdyumov AV, Lin N, Hsung RP, Gullickson GC, Cole KP, Sydorenko N, Swidorski JJ (2006) Org Lett 8:191

    Article  CAS  Google Scholar 

  33. For recent studies, see: (a) Sagar R, Park J, Koh M, Park SB (2009) J Org Chem 74:2171; (b) Yamamoto Y, Itonaga K (2009) Org Lett 11:717; (c) Hubert C, Moreau J, Batany J, Duboc A, Hurvois J-P, Renaud J-L (2008) Adv Synth Catal 350:40; (d) Brioche JCR, Goodenough KM, Whatrup DJ, Harrity JPA (2008) J Org Chem 73:1946; (e) Brioche JCR, Goodenough KM, Whatrup DJ, Harrity JPA (2007) Org Lett 9:3491; (f) Epstein OL, Rovis T (2006) J Am Chem Soc 128:16480

    Google Scholar 

  34. Also see: (a) Appendino G, Cravotto G, Tagliapietra S, Nano GM, Palmisano G (1990) Helv Chim Acta 73:1865; (b) Schuda PF, Price WA (1987) J Org Chem 52:1972; (c) de March P, Moreno-Mañas M, Casado J, Pleixats R, Roca JL (1984) J Heterocycl Chem 21:85; (d) Tietze LF, v. Kiedrowski G, Berger B (1982) Synthesis 683; (e) de Groot A, Jansen BJM (1975) Tetrahedron Lett 16:3407

    Google Scholar 

  35. For the earliest work on oxa-[3+ 3] annulations, see: Ikawa M, Stahmann MA, Link KP (1944) J Am Chem Soc 66:902

    Google Scholar 

  36. For applications in natural product syntheses, see: (a) Yamashita S, Iso K, Kitajima K, Himura M, Hirama M (2011) J Org Chem 76:2408; (b) Brioche JCR, Goodenough KM, Whatrup DJ, Harrity JPA (2007) Org Lett 9:3941; (c) Kurdyumov AV, Hsung RP (2006) J Am Chem Soc 128:6272; (d) Liu H, Siegel DR, Danishefsky SJ (2006) Org Lett 8:423; (e) Olson BS, Trauner D (2005) Synlett 700; (f) Malerich JP, Maimone TJ, Elliott GI, Trauner D (2005) J Am Chem Soc 127:6276; (g) Sunazuka T, Handa M, Nagai K, Shirahata T, Harigaya Y, Otoguro K, Kuwajima I, Õmura S (2004) Tetrahedron 60:7845; (h) Kurdyumov AV, Hsung RP, Ihlen K, Wang J (2003) Org Lett 5:3935; (i) Hsung RP, Cole KP, Zehnder LR, Wang J, Wei L-L, Yang X-F, Coverdale HA (2003) Tetrahedron 59:311; (j) Malerich JP, Trauner D (2003) J Am Chem Soc 125:9554; (k) Zehnder LR, Hsung RP, Wang J, Golding GM (2000) Angew Chem Int Ed 39:3876

    Google Scholar 

  37. For a key review on chemistry of 1,3-dicarbonyls, see: Simon C, Constantieux T, Rodriguez J (2004) Eur J Org Chem 4957

    Google Scholar 

  38. For beautiful reviews on tandem reactions, see: (a) Tietze LF (1996) Chem Rev 96:115; (b) Tietze LF, Beifuss U (1993) Angew Chem Int Ed 32:131; (c) Tietze LF (1990) J Heterocycl Chem 27:47

    Google Scholar 

  39. For reviews for pericyclic ring-closures, see: (a) Marvell EN (1980) Thermal electrocyclic reactions. Academic, New York; (b) Okamura WH, de Lera AR (1991) In: Trost BM, Fleming I, Paquette LA (eds) Comprehensive organic synthesis, vol. 5. Pergamo, New York, pp 699–750

    Google Scholar 

  40. For informative reviews on ring-closure in natural product synthesis, see: (a) Beaudry CM, Malerich JP, Trauner D (2005) Chem Rev 105:4757; (b) Pindur U, Schneider GH (1994) Chem Soc Rev 409

    Google Scholar 

  41. For leading references on electrocyclic ring-closures involving 1-oxatrienes, see: (a) Shishido K, Shitara E, Fukumoto K (1985) J Am Chem Soc 107:5810; (b) Shishido K, Hiroya K, Fukumoto K, Kametani T (1986) Tetrahedron Lett 27:971

    Google Scholar 

  42. For a leading review, see: Tang Y, Oppenheimer J, Song Z, You L, Zhang X, Hsung RP (2006) Tetrahedron 62:10785

    Google Scholar 

  43. The term “formal [3 + 3]” was used to describe [3 + 3] carbo-cycloadditions. See: Seebach D, Missbach M, Calderari G, Eberle M (1990) J Am Chem Soc 112:7625

    Google Scholar 

  44. For earlier studies on carbo-[3 + 3] formal cycloadditions and annulations, see: Landesman HK, Stork G (1956) J Am Chem Soc 78:5129

    Google Scholar 

  45. For leading reviews on step-wise carbo-[3 + 3] formal cycloadditions, see: (a) Filippini M-H, Rodriguez J (1999) Chem Rev 99:27; (b) Butkus E (2001) Synlett 1827; (c) Feist H, Langer P (2007) Synthesis 327

    Google Scholar 

  46. For a seminal study, see: de March P, Moreno-Mañas M, Casado J, Pleixats R, Roca JL, Trius A (1984) J Heterocyclic Chem 21:1369

    Google Scholar 

  47. (a) Cole KP, Hsung RP (2003) Org Lett 5:4843; (b) Buchanan GS, Cole KP, Li G, Tang Y, You L, Hsung RP (2011) Tetrahedron 67:10105; (c) Buchanan GS, Cole KP, Tang Y, Hsung RP (2011) J Org Chem 76:7027

    Google Scholar 

  48. For an initial communication on recognition of the unique structural topology of ABD-tricycle 2, see: Cole KP, Hsung RP (2005) Chem Commun 5784

    Google Scholar 

  49. You L, Hsung RP, Bedermann AA, Kurdyumov AK, Tang Y, Buchanan GS, Cole KP (2008) Adv Synth Catal 350:2885

    Article  CAS  Google Scholar 

  50. For an initial communication on completion of our total synthesis of (±)-phomactin A, see: Tang Y, Cole KP, Buchanan GS, Li G, Hsung RP (2009) Org Lett 11:1591

    Google Scholar 

  51. (a) Kozmin SA, Iwama T, Huang Y, Rawal VH (2002) J Am Chem Soc 124:4628; (b) Kozmin SA, Green MT, Rawal VH (1999) J Org Chem 64:8045

    Google Scholar 

  52. (a) Huang Y, Iwama T, Rawal VH (2000) J Am Chem Soc 122:7843; (b) Huang Y, Iwama T, Rawal VH (2002) Org Lett 4:1163; Also see: (c) Kozmin SA, Iwama T, Huang Y, Rawal VH (2002) J Am Chem Soc 124:4628

    Google Scholar 

  53. Huang Y, Iwama T, Rawal VH (2002) J Am Chem Soc 124:5950

    Article  CAS  Google Scholar 

  54. (a) Jacobsen EN (2000) Acc Chem Res 33:421; (b) For application of Cr(III)-salen catalysts in enantioselective hetero-Diels-Alder reactions: Schaus S, Brånalt J, Jacobsen EN (1998) J Org Chem 63:403

    Google Scholar 

  55. Kornblum N, DeLaMare HE (1951) J Am Chem Soc 73:880

    Article  CAS  Google Scholar 

  56. Nicolaou KC, Shi GQ, Gunzer JL, Gartner GP, Yang Z (1997) J Am Chem Soc 119:5467

    Article  CAS  Google Scholar 

  57. Sheppard WA (1968) J Org Chem 33:3297

    Article  CAS  Google Scholar 

  58. Ferezou J-P, Julia M, Li Y, Liu L-W, Pancrazi A, Porteu F (1994) Bull Soc Chim Fr 131:865

    CAS  Google Scholar 

  59. Shiozaki M (1991) J Org Chem 56:528

    Article  CAS  Google Scholar 

  60. Burgess EM, Penton HR, Taylor EA (1970) J Am Chem Soc 92:5244

    Article  Google Scholar 

  61. Dauben WG, Michno DM (1977) J Org Chem 42:682

    Article  CAS  Google Scholar 

  62. Sundararaman P, Werner Herz W (1977) J Org Chem 42:813

    Article  CAS  Google Scholar 

  63. For some examples, see: (a) Gordon MS, Jacob J, Espenson JH, Jensen JH (1998) Organometallics 17:1835; (b) Wang G, Jimtaisong A, Luck RL (2004) Organometallics 23:4522; (c) Osborn JA, Bellemin-Laponnaz S, Gisie H, Le Ny J-P (1997) Angew Chem Int Ed 36:976; (d) Grubbs RH, Morrill C (2005) J Am Chem Soc 127:2842; (e) Osborn JA, Le Ny J-P, Bellemin-Laponnaz S (2000) Tetrahedron Lett 41:1549

    Google Scholar 

  64. For related protocols, see: (a) Boyer F-D, Hanna I (2005) J Org Chem 70:1077; (b) Iranpoor N, Shekarriz M, Shiriny F (1998) Synth Commun 28:347

    Google Scholar 

  65. For a recent example, see: (a) Chai Y, McIntosh MC (2004) Tetrahedron Lett 45:3269; Also see: (b) Sundararaman P, Herz W (1977) J Org Chem 42:813; (c) Chu A, Mander LN (1988) Tetrahedron Lett 29:2727

    Google Scholar 

  66. Wydra H, Paryzek Z (1984) Tetrahedron Lett 25:2601

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Pharmacy and Department of Chemistry, University of Wisconsin – Madison, Madison, WI, 53706, USA

    Yu Tang, Kevin P. Cole & Richard P. Hsung

Authors
  1. Yu Tang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kevin P. Cole
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Richard P. Hsung
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Firestone Court 3, Skillman, 08558, New Jersey, USA

    Jie Jack Li

  2. , Dept. of Chemistry and Chemical Biology, Harvard University, Oxford Street 12, Cambridge, 02138, USA

    E.J. Corey

Rights and permissions

Reprints and permissions

Copyright information

© 2012 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Tang, Y., Cole, K.P., Hsung, R.P. (2012). Phomactin A. In: Li, J., Corey, E. (eds) Total Synthesis of Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-34065-9_8

Download citation

Publish with us

Policies and ethics

Search

Navigation