Toward an enantioselective total synthesis of sarain A: construction of an advanced intermediate and rearrangement of the sarain A core under mild conditions

Christopher J Douglas; Sheldon Hiebert; Larry E Overman

doi:10.1021/ol050038m

Toward an enantioselective total synthesis of sarain A: construction of an advanced intermediate and rearrangement of the sarain A core under mild conditions

Org Lett. 2005 Mar 3;7(5):933-6. doi: 10.1021/ol050038m.

Authors

Christopher J Douglas¹, Sheldon Hiebert, Larry E Overman

Affiliation

¹ Department of Chemistry, University of California-Irvine, 516 Rowland Hall, Irvine, CA 92697-2025, USA.

PMID: 15727478
DOI: 10.1021/ol050038m

Abstract

A high-yielding N-sulfonyliminium ion-enoxysilane cyclization and a ring-closing metathesis are key steps in the enantioselective synthesis of late-stage intermediates en route to sarain A. Also revealed is an unprecedented rearrangement of the tetracyclic sarain A core under mildly acidic conditions. [structure: see text]

Publication types

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

MeSH terms

Bridged-Ring Compounds / chemical synthesis*
Bridged-Ring Compounds / chemistry*
Catalysis
Cyclization
Indicators and Reagents
Molecular Structure
Stereoisomerism

Substances

Bridged-Ring Compounds
Indicators and Reagents
sarain A

Grants and funding

HL 25854/HL/NHLBI NIH HHS/United States