Total synthesis of (-)-callystatin A

Organic Letters
N F Langille, James S Panek

Abstract

[reaction: see text] A convergent enantioselective synthesis of the natural product (-)-callystatin A (1) is described. Key features of the synthesis include a lipase-mediated kinetic resolution to install the C5 lactone stereochemistry, a hydrozirconation-based approach to the C8-C9 trisubstituted (Z)-olefin, and a stereoselective cross-coupling of a vinyl dibromide to install the C14-C15 trisubstituted (E)-olefin.

References

Sep 28, 2001·Organic Letters·M KalesseA Saeed
Apr 27, 2002·The Journal of Organic Chemistry·James A Marshall, Matthew P Bourbeau

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Citations

Nov 17, 2011·Chemical Reviews·Giorgio Chelucci
Feb 3, 2006·Natural Product Reports·Gillian M Nicholas, Andrew J Phillips
Sep 8, 2006·Organic Letters·James A Marshall, Ann M Mikowski
Nov 8, 2005·Bioorganic & Medicinal Chemistry Letters·James A MarshallFrederick Valeriote
Apr 2, 2015·Organic & Biomolecular Chemistry·Sadagopan Raghavan, Sheelamanthula Rajendar
Sep 25, 2015·Cells·Achim DickmannsRalf Ficner
Oct 6, 2007·Angewandte Chemie·Simone BonazziKarl Gademann
Sep 29, 2012·Chemistry : a European Journal·Mathieu CandyCyril Bressy
Sep 22, 2009·Angewandte Chemie·Takahiro NishimuraTamio Hayashi
Jan 1, 2010·European Journal of Organic Chemistry·Holly A ReichardGlenn C Micalizio
Feb 22, 2011·Chemistry : a European Journal·Marion BarbazangesPeter Turner
Sep 4, 2008·Angewandte Chemie·Holly A ReichardGlenn C Micalizio
Jan 31, 2012·Organic & Biomolecular Chemistry·Sandip A Pujari, Krishna P Kaliappan

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