A formal synthesis of (-)-mycalamide A

Barry M Trost; Hanbiao Yang; Gary D Probst

doi:10.1021/ja038787r

A formal synthesis of (-)-mycalamide A

J Am Chem Soc. 2004 Jan 14;126(1):48-9. doi: 10.1021/ja038787r.

Authors

Barry M Trost¹, Hanbiao Yang, Gary D Probst

Affiliation

¹ Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu

PMID: 14709053
DOI: 10.1021/ja038787r

Abstract

Novel strategies are developed for an efficient formal synthesis of (-)-mycalamide A. The left-hand side (-)-7-benzoylpederic acid is synthesized from (2S,3S)-2,3-epoxybutane. The key features include a highly regioselective Ru-catalyzed alkene-alkyne coupling reaction and a novel way to control the challenging C(7) stereocenter. The right-hand side was synthesized from (R)-pantolactone. The complex trioxodecalin core is constructed with two Pd(0)-catalyzed O-pi-allyl cyclizations. The first one is chemoselective, while the second one is highly diastereoselective. Three additional steps would be required to complete a total synthesis of (-)-mycalamide A.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Animals
Marine Toxins / chemical synthesis
Porifera / chemistry
Pyrans / chemical synthesis*
Stereoisomerism

Substances

Marine Toxins
Pyrans
mycalamide A

Grants and funding

GM 13598/GM/NIGMS NIH HHS/United States