Enantioselective total synthesis of (+)-testudinariol a using a new nickel-catalyzed allenyl aldehyde cyclization

Kande K D Amarasinghe; John Montgomery

doi:10.1021/ja027148y

Enantioselective total synthesis of (+)-testudinariol a using a new nickel-catalyzed allenyl aldehyde cyclization

J Am Chem Soc. 2002 Aug 14;124(32):9366-7. doi: 10.1021/ja027148y.

Authors

Kande K D Amarasinghe¹, John Montgomery

Affiliation

¹ Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA.

PMID: 12167019
DOI: 10.1021/ja027148y

Abstract

An enantioselective total synthesis of (+)-testudinariol A was completed. A new nickel-catalyzed allenyl aldehyde cyclization was developed in the approach. In addition, an asymmetric anti aldol reaction and a two-directional oxocarbenium ion/vinyl silane condensation were employed as key steps.

Publication types

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

MeSH terms

Aldehydes / chemistry*
Catalysis
Nickel / chemistry*
Stereoisomerism
Triterpenes / chemical synthesis*

Substances

Aldehydes
Triterpenes
testudinariol A
Nickel

Grants and funding

GM 57014/GM/NIGMS NIH HHS/United States