Concise synthesis of PM-94128 and Y-05460M-A

Masaru Enomoto; Shigefumi Kuwahara

doi:10.1021/jo9014968

Concise synthesis of PM-94128 and Y-05460M-A

J Org Chem. 2009 Oct 2;74(19):7566-9. doi: 10.1021/jo9014968.

Authors

Masaru Enomoto¹, Shigefumi Kuwahara

Affiliation

¹ Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.

PMID: 19722511
DOI: 10.1021/jo9014968

Abstract

The enantioselective total synthesis of PM-94128, a potent cytotoxin of microbial origin, was accomplished by a concise nine-step sequence of reactions in 14% overall yield from N-Boc-l-leucine. The synthesis of Y-05460M-A, a one-carbon lower homologue of PM-94128, was also achieved from N-Boc-l-valine by the same approach, which enabled its stereochemical determination.

Publication types

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

MeSH terms

Chromones / chemical synthesis*
Chromones / chemistry
Coumarins / chemical synthesis*
Coumarins / chemistry
Molecular Conformation
Stereoisomerism

Substances

Chromones
Coumarins
PM 94128
Y 05460M-A