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


Kortet, Sami; Claraz, Aurélie; Pihko, Petri M. (2020). Catalytic Enantioselective Total Synthesis of (+)–Lycoperdic Acid. Organic Letters, 22 (8), 3010-3013. DOI: 10.1021/acs.orglett.0c00772


JYU authors or editors


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: http://doi.org/10.1021/acs.orglett.0c00772

Open Access: Publication channel is not openly available

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


Contributing organizations


Related projects


Ministry reporting: Yes

Reporting Year: 2020

Preliminary JUFO rating: 2


Last updated on 2020-18-08 at 13:05