Synthesis of Immunomodulatory Marine Natural Products

Danishefsky, S. J.; Inoue, M.; Trauner, D.

doi:10.1007/978-3-662-04042-3_1

S. J. Danishefsky,
M. Inoue &
D. Trauner

Part of the book series: Ernst Schering Research Foundation Workshop ((SCHERING FOUND,volume 32))

227 Accesses
1 Citations

Abstract

There has been a long-term fruitful synergy between the study of organic chemistry and the quest for the identification of novel and potentially valuable products from nature (Barton and Nakanishi 1999). Following the isolation of such naturally derived agents, chemistry has provided the indispensable intellectual framework for structure elucidation. In the early days, these assignments were accomplished through the medium of classical degradative chemistry. The validity of chemistry-based structure deduction was extremely dependent on the powerful logic which unifies the basic reactions of organic chemistry and allows for organization and interpretation of reaction sequences.

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)

eBook: USD 39.99; Price excludes VAT (USA)

Softcover Book: USD 54.99; Price excludes VAT (USA)

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

References

Arimoto H, Hayakawa I, Kuramoto M, Uemura D (1998) Tetrahedron Lett 39:861–862
Article CAS Google Scholar
Balog A, Harris C, Savin K, Zhang K-G, Chou T-C, Danishefsky SJ (1998) Angew Chem Int Ed Engl 37:2675–2678
Article CAS Google Scholar
Barclay AN, Brown MH, Law SKA, McKnight AJ, Tomlinson MG, Van der Merwe PA (1997) The leucocyte antigen facts book. Academic, Oxford Barton DHR, Nakanishi K (eds) (1999) Comprehensive natural products chemistry. Elsevier, Amsterdam
Google Scholar
Boden EP, Keck GE (1985) J Org Chem 50:2394–2395
Article CAS Google Scholar
Burgess LE, Meyers AI (1991) J Am Chem Soc 113:9858–9859
Article CAS Google Scholar
Carlos TM, Harlan JK (1994) Blood 84:2068–2101
Google Scholar
Corey EJ, Myers AG (1985) J Am Chem Soc 107:5574–5576
Article CAS Google Scholar
Corey EJ, Tius MA, Das J (1980) J Am Chem Soc 102:1742–1744
Article CAS Google Scholar
Danheiser RL, Halgason AL (1994) J Am Chem Soc 116:9471–9479
Article CAS Google Scholar
Ennis MD, Hoffman RL, Ghazal NB, Old DW, Mooney PA (1996) J Org Chem 61:5813–5817
Article CAS Google Scholar
Faulkner DJ (1999) Nat Prod Rep 16:155–198
Article Google Scholar
Feutrill GI, Mirrington RN (1972) Aust J Chem 25:1719–1729
Article CAS Google Scholar
Fürstner A (1999) Chem Rev 99:991–1045
Article PubMed Google Scholar
Fürstner A, Konetzki I (1998) J Org Chem 63:3072–3080
Article Google Scholar
Foster CA (1996) J Allergy Clin Immunol S272-S277
Google Scholar
Frontier AJ (1999) PhD thesis, Columbia University
Google Scholar
Fujiwara T, Iwasaki T, Takeda T (1993) Chem Lett 1321–1324
Google Scholar
Gilbert JC, Weerasooriya U (1979) J Org Chem 44:4997–4998
Article CAS Google Scholar
Godfrey AG, Ganem B (1992) Tetrahedron Lett 33:7461–7464
Article CAS Google Scholar
Grigg R, Teasdale A, Sridharan V (1991) Tetrahedron Lett 32:3859–3862
Article CAS Google Scholar
Guerriero A, Cuomo V, Vanzanella F, Pietra F (1990) Helv Chim Acta 3:2090–2096
Article Google Scholar
Guevel AC, Hart DJ (1996) J Org Chem 61:465–472
Article PubMed CAS Google Scholar
Hagiwara H, Uda H, Kodama T (1980) J Chem Soc Perkin Trans 1:963–977
Article Google Scholar
Hallock YF, Cardellina IIJH, Boyd MR (1998) Nat Prod Lett 11:153–160
Article CAS Google Scholar
Hiemstra H, Speckamp WN (1991) In: Trost BM, Fleming I (eds) Comprehensive organic synthesis, vol 2, chap 4.5. Pergamon, Oxford
Google Scholar
Hock RC, Schraustätter IU, Cochrane CG (1996) J Lab Clin Med 128:134–145
Article Google Scholar
Huang AX, Xiong Z, Corey EJ (1999) J Am Chem Soc 121:9999–10003
Article CAS Google Scholar
Inoue M, Frontier AJ, Danishefsky SJ (2000) Angew Chem Int Ed (in press)
Google Scholar
Johnson CR, Braun MP (1993) J Am Chem Soc 115:11014–11015
Article CAS Google Scholar
Jones AB, Villalobos A, Linde RG, Danishefsky SJ (1990) J Org Chem 55:2786–2797
Article CAS Google Scholar
Jones G (1997) Org React 49:1–330
CAS Google Scholar
Keen SP, Weinreb SM (1998) J Org Chem 63:6739–6741
Article CAS Google Scholar
Kelly TR, Li Q, Bhushan V (1990) Tetrahedron Lett 31:161–164
Article CAS Google Scholar
Kinney WA, Coghlan MJ, Paquette LA (1985) J Am Chem Soc 107:7352–7360
Article CAS Google Scholar
Knight DW (1991) In: Trost BM, Fleming I (eds) Comprehensive organic synthesis, vol 3. Pergamon, Oxford, pp 481–520
Chapter Google Scholar
Koch AE, Halloran MM, Haskell CJ, Shah MR, Polverini PJ (1995) Nature 376:517–519
Article PubMed CAS Google Scholar
Kuramoto M, Tong C, Yamada K, Chiba T, Hayashi Y, Uemura D (1996) Tetrahedron Lett 37:3867–3870
Article CAS Google Scholar
Kurbanov M, Semenovsky AV, Smit WA, Shmelev LV, Kucherov VF (1972) Tetrahedron Lett 22:2175–2178
Article Google Scholar
Kwee L (1995) Development 121:489–503
PubMed CAS Google Scholar
Landelle H, Godard AM, Laduree D, Chenu E, Robba M (1991) Chem Pharm Bull 39:3057–3060
Article CAS Google Scholar
Ley SV, Norman J, Griffith WP, Marsden SP (1994) Synthesis 639–666
Google Scholar
Meng D, Bertinato P, Balog A, Su D-S, Kamenecka T, Sorenson E, Danishefsky SJ (1997) J Am Chem Soc 119:10073–10092
Article CAS Google Scholar
Meyers AI, Brengel GP (1997) J Chem Soc Chem Commun 1–8
Google Scholar
Meyers AI, Tschantz MA, Brengel GP (1995) J Org Chem 60:4359–4362
Article CAS Google Scholar
Miller E, Cohen A, Nagos S, Griffith D, Maunder T, Martin T, Weiner-Kronish J, Sticherling M, Christophers E, Matthay M (1992) Am Rev Respir Dis 146:427–432
Article PubMed CAS Google Scholar
Miyaura N, Suzuki A (1995) Chem Rev 95:2457–2483
Article CAS Google Scholar
Mori M, Kaneta N, Shibasaki M (1991) J Org Chem 56:3486–3493
Article CAS Google Scholar
Ohba M, Kawase N, Fujii T (1996) J Am Chem Soc 118:8250–8257
Article CAS Google Scholar
Omodani T, Shishido K (1994) Chem Commun 2781–2782
Google Scholar
Ono N, Kaji A (1986) Synthesis 693–704
Google Scholar
Patil AD, Frey er AJ, Killmer L, Offen P, Carte B, Jurewicz AJ, Johnson RK (1997) Tetrahedron 53:5047–5060
Article CAS Google Scholar
Ragan JA, Claffey MC (1995) Heterocycles 41:57–70
Article CAS Google Scholar
Ranganathan D, Rao CB, Ranganathan S, Mehrotra AK, Iyengar R (1980) J Org Chem 45:1185–1189
Article CAS Google Scholar
Rao M, McGuigan MA, Zhang X, Shaked Z, Kinney WA, Bulliard M, Laboue B, Lee NE (1997) J Org Chem 62:4541–4545
Article PubMed CAS Google Scholar
Romo D., Meyers AI (1991) Tetrahedron 47:9503–9569
Article CAS Google Scholar
Sasaki M, Fuwa H, Inoue M, Tachibana K (1998) Tetrahedron Lett 39:9027–9030
Article CAS Google Scholar
Sato C, Ikeda S, Shirahama H, Matsumoto T (1982) Tetrahedron Lett 23:2099–2102
Article CAS Google Scholar
Scitz M, Dewald B, Gerber N, Baggiolini M (1991) J Clin Invest 87:463–469
Article Google Scholar
Sharmma M, Rodrigues HR (1968) Tetrahedron 24:6583–6589
Article Google Scholar
Soai K, Niwa S (1992) Chem Rev 92:833–856
Article CAS Google Scholar
Soai K, Takahashi K (1994) J Chem Soc Perkin Trans 1:1257–1258
Article Google Scholar
Springer TA (1994) Cell 76:301–314
Article PubMed CAS Google Scholar
Tebbe FN, Marshall GW, Reddy GS (1978) J Am Chem Soc 100:3611–3613
Article CAS Google Scholar
Trauner D, Danishefsky SJ (1999) Tetrahedron Lett 40:6513–6516
Article CAS Google Scholar
Trauner D, Schwarz J, Danishefsky S J (1999) Angew Chem Int Ed 38:3542–3545
Article CAS Google Scholar
Tsuzuki S, Toyama-Sorimachi N, Kitamura F, Tobita Y, Miyasaka M (1998) FEBS Lett 430:414–418
Article PubMed CAS Google Scholar
Weber AE, Steiner MG, Krieter PA, Coletti AE, Tata JR, Halgren TA, Ball RG, Doyle JJ, Schorn TW, Stearns RA, Miller RR, Siegl PKS, Greenlee WJ, Patchett AA (1992) J Med Chem 35:3755–3773
Article PubMed CAS Google Scholar
White JD, Amedio JC, Gut S, Ohira S, Jayasinghe LR (1992) J Org Chem 57:2270–2284
Article CAS Google Scholar
Wipf P, Coish PDG (1997) Tetrahedron Lett 38:5073–5076
Article CAS Google Scholar
Wipf P, Ribe S (1998) J Org Chem 63:6454–6455
Article CAS Google Scholar
Wipf P, Xu W (1994) Tetrahedron Lett 35:5197–5200
Article CAS Google Scholar
Witschel MC, Bestmann HJ (1997) Synthesis 107–112
Google Scholar
Zhang W, Robins MJ (1992) Tetrahedron Lett 33:1177–1180
Article CAS Google Scholar

Download references

Authors

S. J. Danishefsky
View author publications
You can also search for this author in PubMed Google Scholar
M. Inoue
View author publications
You can also search for this author in PubMed Google Scholar
D. Trauner
View author publications
You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

Institut für Organische Chemie, Universität Wien, Währinger Str. 38, 1090, Wien, Austria
J. Mulzer
Preclinical Drug Research, Schering AG, Müllerstr. 178, 13342, Berlin, Germany
R. Bohlmann

Rights and permissions

Reprints and permissions

Copyright information

About this paper

Cite this paper

Danishefsky, S.J., Inoue, M., Trauner, D. (2000). Synthesis of Immunomodulatory Marine Natural Products. In: Mulzer, J., Bohlmann, R. (eds) The Role of Natural Products in Drug Discovery. Ernst Schering Research Foundation Workshop, vol 32. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-04042-3_1

Download citation

DOI: https://doi.org/10.1007/978-3-662-04042-3_1
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-04044-7
Online ISBN: 978-3-662-04042-3
eBook Packages: Springer Book Archive

Publish with us

Policies and ethics