Synthetic study toward the total synthesis of maoecrystal V

Jianxian Gong; Guang Lin; Chuang-chuang Li; Zhen Yang

doi:10.1021/ol9014392

Synthetic study toward the total synthesis of maoecrystal V

Org Lett. 2009 Nov 5;11(21):4770-3. doi: 10.1021/ol9014392.

Authors

Jianxian Gong¹, Guang Lin, Chuang-chuang Li, Zhen Yang

Affiliation

¹ Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055, China.

PMID: 19863143
DOI: 10.1021/ol9014392

Abstract

A novel and concise approach for the construction of the core structure of maoecrystal V (1) has been developed. Utilizing the lead-mediated arylation of beta-ketoesters and oxidative dearomatization/IMDA reaction as key steps, the two consecutive all-carbon quaternary centers (C-9 and C-10) were constructed in a stereoselective manner. The developed chemistry paves the way for the total synthesis of this fascinating natural product.

Publication types

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

MeSH terms

Catalysis
Crystallography, X-Ray
Cyclization
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Diterpenes / pharmacology
Drugs, Chinese Herbal / chemical synthesis
Drugs, Chinese Herbal / chemistry
Drugs, Chinese Herbal / pharmacology
Isodon / chemistry
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Stereoisomerism

Substances

Diterpenes
Drugs, Chinese Herbal
maoecrystal A