Formal total synthesis of N-methylmaysenine

Lin Wang; Jianxian Gong; Lujiang Deng; Zheng Xiang; Zhixing Chen; Yuefan Wang; Jiahua Chen; Zhen Yang

doi:10.1021/ol900384u

Formal total synthesis of N-methylmaysenine

Org Lett. 2009 Apr 16;11(8):1809-12. doi: 10.1021/ol900384u.

Authors

Lin Wang¹, Jianxian Gong, Lujiang Deng, Zheng Xiang, Zhixing Chen, Yuefan Wang, Jiahua Chen, Zhen Yang

Affiliation

¹ Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, and Laboratory of Chemical Genomics, Shenzhen Graduate School, Peking University, Beijing 100871, China.

PMID: 19296671
DOI: 10.1021/ol900384u

Abstract

A novel synthetic approach for the formal total synthesis of N-methylmaysenine (1) has been developed. Key steps involve the Ti-mediated vinylogous Mukaiyama aldol reaction of chiral ketene silyl N,O-acetal with beta-dithiane-substituted aldehyde, an aldol condensation, and a ring-closing metathesis reaction.

Publication types

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

MeSH terms

Aldehydes / chemistry*
Catalysis
Cyclization
Maytansine / analogs & derivatives*
Maytansine / chemical synthesis
Maytansine / chemistry
Molecular Structure

Substances

Aldehydes
N-methylmaysenine
Maytansine
3-hydroxybutanal