A1 Journal article (refereed)
Catalytic Enantioselective Total Synthesis of (+)–Lycoperdic Acid (2020)

Kortet, S., Claraz, A., & Pihko, P. M. (2020). Catalytic Enantioselective Total Synthesis of (+)–Lycoperdic Acid. Organic Letters, 22(8), 3010-3013. https://doi.org/10.1021/acs.orglett.0c00772

JYU authors or editors

Kortet, Sami
Claraz, Aurélie
Pihko, Petri

Publication details

All authors or editors: Kortet, Sami; Claraz, Aurélie; Pihko, Petri M.

Journal or series: Organic Letters

ISSN: 1523-7060

eISSN: 1523-7052

Publication year: 2020

Volume: 22

Issue number: 8

Pages range: 3010-3013

Publisher: American Chemical Society

Publication country: United States

Publication language: English

DOI: https://doi.org/10.1021/acs.orglett.0c00772

Publication open access: Not open

Publication channel open access:

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/68735

Abstract

A concise enantio- and stereocontrolled synthesis of (+)-lycoperdic acid is presented. The stereochemical control is based on iminium-catalyzed Mukaiyama–Michael reaction and enamine-catalyzed organocatalytic α-chlorination steps. The amino group was introduced by azide displacement, affording the final stereochemistry of (+)-lycoperdic acid. Penultimate hydrogenation and hydrolysis afforded pure (+)-lycoperdic acid in seven steps from a known silyloxyfuran.

Keywords: amino acids; chemical synthesis; catalysis

Fields of science: