A concise total synthesis of (-)-maoecrystal Z

Jacob Y Cha; John T S Yeoman; Sarah E Reisman

doi:10.1021/ja2073356

A concise total synthesis of (-)-maoecrystal Z

J Am Chem Soc. 2011 Sep 28;133(38):14964-7. doi: 10.1021/ja2073356. Epub 2011 Aug 30.

Authors

Jacob Y Cha¹, John T S Yeoman, Sarah E Reisman

Affiliation

¹ Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

PMID: 21877709
DOI: 10.1021/ja2073356

Abstract

The first total synthesis of (-)-maoecrystal Z is described. The key steps of the synthesis include a diastereoselective Ti(III)-mediated reductive epoxide coupling reaction and a diastereoselective Sm(II)-mediated reductive cascade cyclization reaction. These transformations enabled the preparation of (-)-maoecrystal Z in only 12 steps from (-)-γ-cyclogeraniol.

Publication types

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

MeSH terms

Diterpenes, Kaurane / chemical synthesis*
Diterpenes, Kaurane / chemistry
Molecular Conformation
Stereoisomerism

Substances

Diterpenes, Kaurane
maoecrystal Z