First total synthesis of (+)-epogymnolactam, a novel autophagy inducer

Yuji Okado; Kengo Shigetomi; Shinya Mitsuhashi; Makoto Ubukata

doi:10.1038/ja.2015.63

First total synthesis of (+)-epogymnolactam, a novel autophagy inducer

J Antibiot (Tokyo). 2015 Dec;68(12):721-4. doi: 10.1038/ja.2015.63. Epub 2015 May 27.

Authors

Yuji Okado¹, Kengo Shigetomi¹, Shinya Mitsuhashi¹, Makoto Ubukata¹

Affiliation

¹ Research Faculty of Agriculture, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.

PMID: 26014720
DOI: 10.1038/ja.2015.63

Abstract

A novel autophagy inducer, (+)-epogymnolactam (1), was first synthesized from cis-4-benzyloxy-2-butene-1-ol (2) in eight steps. A reliable preparation of optically pure epoxy alcohol (+)-3 from monobenzyl derivative (2) was established by a tandem strategy, Sharpless epoxidation/lipase kinetic resolution.

Publication types

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

MeSH terms

Autophagy / drug effects*
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / chemistry
Stereoisomerism

Substances

Bridged Bicyclo Compounds, Heterocyclic
epogymnolactam