Total Synthesis of (6S, 1'S, 2, R)-6-(1', 2, -Dihydroxypentyl)-4-methoxy-5, 6-dihydropyrane-2-one (LL-P880/J) and Its C6-Epimer, a Fungal Metabolite from Penicillium sp.

Mitsunori KIRIHATA; Kazunari OHTA; Itsuo ICHIMOTO; Hiroo UEDA

doi:10.1271/bbb1961.54.2401

Agricultural and Biological Chemistry

Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369

Total Synthesis of (6S, 1'S, 2, R)-6-(1', 2, -Dihydroxypentyl)-4-methoxy-5, 6-dihydropyrane-2-one (LL-P880/J) and Its C₆-Epimer, a Fungal Metabolite from Penicillium sp.

Mitsunori KIRIHATA, Kazunari OHTA, Itsuo ICHIMOTO, Hiroo UEDA

Author information

JOURNAL FREE ACCESS

1990 Volume 54 Issue 9 Pages 2401-2405

DOI https://doi.org/10.1271/bbb1961.54.2401

Details

Abstract

A fungal metabolite, (6S, 1'S, 2'R)-6-(1', 2'-dihydroxypentyl)-4-methoxy-5, 6-dihydropyrane-2-one (LL-P88β, I), and its C₆-epimer (II) were synthesized by the chiron approach. The key intermediate, (2S, 3R)-2, 3-dihydroxyhexanal derivative (3), was prepared from D-glucose as a chiral building block and reacted with the dianion of ethyl acetoacetate to complete the formal syntheses of I and II.

Content from these authors

This article cannot obtain the latest cited-by information.

Favorites & Alerts

Corresponding author

Register with J-STAGE for free!