Skip to main content

Combined Iminium-Enamine Catalyzed Approaches

  • Chapter
  • First Online:
  • 1354 Accesses

Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 96))

Abstract

The field of natural product syntheses has been dominated by (transition-) metal catalyzed asymmetric reactions for decades. However, besides the very broad range of different transformations that can be achieved by metal catalysis, the use of substoichiometric amounts of small-organic molecule catalysts (organocatalysis) has proved also to possess an enormous potential for a variety of reactions. Over the last few years numerous impressive examples on the use of organocatalysts in the syntheses of complex natural products and other biologically active molecules have been reported. Very often these reactions have resulted in a significant reduction of reaction steps, leading to more efficient and elegant routes.

The intention of this contribution is to provide the reader with an illustrative overview concerning successful and widely used applications of organocatalysis in the field of natural product synthesis. The main focus will be on organocatalytic key-steps for each (multi-step) synthesis described, whereas other often particularly innovative transformations will be omitted, as this would be beyond the scope of this volume.

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

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   219.99
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

Learn about institutional subscriptions

References

  1. Marques-Lopez E, Herrera RP, Christmann M (2010) Asymmetric organocatalysis in total synthesis – a trial by fire. Nat Prod Rep 27:1138

    Article  CAS  Google Scholar 

  2. Grondal C, Jeanty M, Enders D (2010) Organocatalytic cascade reactions as a new tool in total synthesis. Nat Chem 2:167

    Article  CAS  Google Scholar 

  3. Mangion IK, MacMillan DWC (2005) Total synthesis of brasoside and littoralisone. J Am Chem Soc 127:3696

    Article  CAS  Google Scholar 

  4. Enders D, Hüttl MRM, Grondal C, Raabe G (2006) Control of four stereocentres in a triple cascade organocatalytic reaction. Nature 441:861

    Article  CAS  Google Scholar 

  5. Alachraf MW, Handayani PP, Hüttl MRM, Grondal C, Enders D, Schrader W (2011) Electrospray mass spectrometry for detailed mechanistic studies of a complex organocatalyzed triple cascade reaction. Org Biomol Chem 9:1047

    Article  CAS  Google Scholar 

  6. Ramachary DB, Jain S (2011) Sequential one-pot combination of multi-component and multi-catalysis cascade reactions: an emerging technology in organic synthesis. Org Biomol Chem 9:1277

    Article  CAS  Google Scholar 

  7. Carpenter J, Northrup AB, Chung D, Wiener JJM, Kim SG, MacMillan DWC (2008) Total synthesis and structural revision of callipeltoside C. Angew Chem Int Ed 47:3568

    Article  CAS  Google Scholar 

  8. Hong BC, Wu MF, Tseng HC, Liao JH (2006) Enantioselective organocatalytic formal [3+3]-cycloaddition of α, β-unsaturated aldehydes and application to the asymmetric synthesis of (–)-isopulegol hydrate and (–)-cubebaol. Org Lett 8:2217

    Article  CAS  Google Scholar 

  9. Hong BC, Nimje RY, Yang CY (2007) The organocatalytic direct self-trimerization of acrolein: application to the total synthesis of montiporyne F. Tetrahedron Lett 48:1121

    Article  CAS  Google Scholar 

  10. Michrowska A, List B (2009) Concise synthesis of ricciocarpin A and discovery of a more potent analogue. Nat Chem 1:225

    Article  CAS  Google Scholar 

  11. Simmons B, Walji AM, MacMillan DWC (2009) Cycle-specific organocascade catalysis: application to olefin hydroamination, hydro-oxidation, and amino-oxidation, and to natural product synthesis. Angew Chem Int Ed 48:4349

    Article  CAS  Google Scholar 

  12. Hong BC, Kotame P, Tsai CW, Liao JH (2010) Enantioselective total synthesis of (+)-conicol via cascade three-component organocatalysis. Org Lett 12:776

    Article  CAS  Google Scholar 

  13. Vanek T, Novotny M, Podlipna R, Saman D, Valterova I (2003) Biotransformation of citronellal by Solanum aviculare suspension cultures: preparation of p-menthane-3,8-diols and determination of their absolute configurations. J Nat Prod 66:1239

    Article  CAS  Google Scholar 

  14. Bae BH, Im KS, Choi WC, Hong JK, Lee CO, Choi JS, Son BW, Song JI, Jung JH (2000) New acetylenic compounds from the stony coral Montipora sp. J Nat Prod 63:1511

    Article  CAS  Google Scholar 

  15. Wurzel G, Becker H (1990) Sesquiterpenoids from the liverwort Ricciocarpos natans. Phytochemistry 29:2565

    Article  CAS  Google Scholar 

  16. Zinsmeister HD, Becker H, Eicher T (1991) Bryophytes, a source of biologically active, naturally occurring material. Angew Chem Int Ed 30:130

    Article  Google Scholar 

  17. Garrido L, Zubia E, Ortega MJ, Salva J (2002) New meroterpenoids from the ascidian Aplidium conicum. J Nat Prod 65:1328

    Article  CAS  Google Scholar 

  18. Simon-Levert A, Arrault A, Bontemps-Subielos N, Canal C, Banaigs B (2005) Meroterpenes from the ascidian Aplidium aff. densum. J Nat Prod 68:1412

    Article  CAS  Google Scholar 

  19. Walji AM, MacMillan DWC (2007) Strategies to bypass the taxol problem. Enantioselective cascade catalysis, a new approach for the efficient construction of molecular complexity. Synlett 1477

    Google Scholar 

  20. Beechan CM, Djerassi C, Eggert H (1978) Terpenoids 74. Sesquiterpenes from soft coral Sinularia mayi. Tetrahedron 34:2503

    Article  CAS  Google Scholar 

  21. Moreira IC, Lago JHG, Young MCM, Roque NF (2003) Antifungal aromadendrane sesquiterpenoids from the leaves of Xylopia brasiliensis. J Brazil Chem Soc 14:828

    Article  CAS  Google Scholar 

  22. Wu TS, Chan YY, Leu YL (2000) The constituents of the root and stem of Aristolochia heterophylla Hemsl. Chem Pharm Bull 48:357

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 2012 Springer-Verlag/Wien

About this chapter

Cite this chapter

Waser, M. (2012). Combined Iminium-Enamine Catalyzed Approaches. In: Asymmetric Organocatalysis in Natural Product Syntheses. Progress in the Chemistry of Organic Natural Products, vol 96. Springer, Vienna. https://doi.org/10.1007/978-3-7091-1163-5_4

Download citation

Publish with us

Policies and ethics