Enantioselective deprotonation of meso-cycloheptanone derivative: application to the synthesis of a potential intermediate for pseudomonic acid B

Toshio Honda; Nobuaki Kimura

doi:10.1021/ol027192i

Enantioselective deprotonation of meso-cycloheptanone derivative: application to the synthesis of a potential intermediate for pseudomonic acid B

Org Lett. 2002 Dec 12;4(25):4567-70. doi: 10.1021/ol027192i.

Authors

Toshio Honda¹, Nobuaki Kimura

Affiliation

¹ Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan. honda@hoshi.ac.jp

PMID: 12465939
DOI: 10.1021/ol027192i

Abstract

[reaction: see text] A novel synthetic path to a potential intermediate for the synthesis of pseudomonic acid B was established by employing enantioselective deprotonation of a meso-cycloheptanone derivative bearing hydroxy groups at the 3,4,5,6-positions with lithium (S,S')-alpha,alpha'-dimethyldibenzylamide as a key step.

Publication types

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

MeSH terms

Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis
Anti-Inflammatory Agents, Non-Steroidal / chemistry
Fatty Acids / chemical synthesis*
Fatty Acids / chemistry
Lactones / chemical synthesis
Lactones / chemistry
Molecular Structure
Stereoisomerism
Sulfones

Substances

Anti-Inflammatory Agents, Non-Steroidal
Fatty Acids
Lactones
Sulfones
rofecoxib
pseudomonic acid I