Enantio and diastereoselective total synthesis of all four stereoisomers of germicidin N

Abstract

Germicidin N (3-ethyl-4-hydroxy-6-[(1S, 2 R)−2-hydroxy-1-methylpropyl]-2H-pyran-2-one, 1), a new α-pyrone from the extracts of a Streptomyces sp. derived from marine algae, has been synthesized for the first time as four possible diastereomers from chiral β-hydroxyester ((S)−6 and (R)−9) through the stereoselective alkylation, Claisen condensation followed by cyclization in a straightforward manner.

Graphical Abstract

Keywords:

• Enantioselective synthesis
• germicidin N
• marine algae
• α-pyrone
• quorum sensing activity

Additional information

Funding

This work was financially supported by JSPS KAKENHI Grant Number [25410051 and 17K07776].