Concise enantiospecific total synthesis of tubingensin A

Adam E Goetz; Amanda L Silberstein; Michael A Corsello; Neil K Garg

doi:10.1021/ja501142e

Concise enantiospecific total synthesis of tubingensin A

J Am Chem Soc. 2014 Feb 26;136(8):3036-9. doi: 10.1021/ja501142e. Epub 2014 Feb 18.

Authors

Adam E Goetz¹, Amanda L Silberstein, Michael A Corsello, Neil K Garg

Affiliation

¹ Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.

Abstract

We report the enantiospecific total synthesis of (+)-tubingensin A. Our synthesis features an aryne cyclization to efficiently introduce the vicinal quaternary stereocenters of the natural product and proceeds in only nine steps (longest linear sequence) from known compounds.

Publication types

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

MeSH terms

Alkaloids / chemistry*
Carbazoles / chemistry*
Cyclization
Molecular Structure
Stereoisomerism

Substances

Alkaloids
Carbazoles

Abstract

Publication types

MeSH terms

Substances

Grants and funding