Synthesis of both enantiomers of lycoperdic acid, an unusual mushroom-derived amino acid-Reference-Cited by-同舟云学术

Synthesis of both enantiomers of lycoperdic acid, an unusual mushroom-derived amino acid

Published:2021-01 Issue:1 Volume:85 Page:154-159
ISSN:1347-6947
Container-title:Bioscience, Biotechnology, and Biochemistry
language:en
Short-container-title:

Author:

Katsuta Ryo¹^ORCID,Ishiuchi Ryutaro²,Kunisawa Mikiko³,Yajima Arata¹^ORCID,Ishigami Ken¹^ORCID,Nukada Tomoo¹

Affiliation:

1. Department of Chemistry for Life Sciences and Agriculture, Tokyo University of Agriculture, Setagaya-ku, Tokyo, Japan

2. Graduate School of Agriculture, Tokyo University of Agriculture, Setagaya-ku, Tokyo, Japan

3. Department of Fermentation Science, Tokyo University of Agriculture, Setagaya-ku, Tokyo, Japan

Abstract

Abstract An efficient synthesis of both enantiomers of lycoperdic acid, a 4-hydroxyglutamic acid derivative from edible mushroom Lycoperdon perlatum, was achieved from a chiral aminoalcohol. The key steps were a stereoselective introduction of a C3 unit into a bicyclic ketone and oxidative cleavage of a cyclic vicinal diol into a dicarboxylic acid. This report provides the first synthesis of (−)-lycoperdic acid.

Publisher

Oxford University Press (OUP)

Subject

Organic Chemistry,Molecular Biology,Applied Microbiology and Biotechnology,General Medicine,Biochemistry,Analytical Chemistry,Biotechnology

Link

http://academic.oup.com/bbb/article-pdf/85/1/154/36668993/zbaa027.pdf

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1. Total synthesis of lycoperdic acid and stereoisomers (part 1): Double asymmetric hydrogenation of a racemic enamide;Tetrahedron;2023-10

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