Total synthesis of optically active lycopladine a by utilizing diastereoselective protection of carbonyl group in a 1,3-cyclohexanedione derivative

Kou Hiroya, Yoshihiro Suwa, Yusuke Ichihashi, Kiyofumi Inamoto, Takayuki Doi

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

We successfully synthesized two enantiomers of bicyclic enones, (7R,7aR)- and (7S,7aS)-9, from the hemiacetal 2a, which we first synthesized from the symmetrical diketone 1a via diastereoselective carbon-oxygen bond formation between one of the carbonyl groups and the chiral alcohol on the C2 side chain in a 2,2-disubstituted 1,3-cycloalkanedione derivative. We also report the total synthesis of natural (+)-lycopladine A [(+)-6] from (7R,7aR)-9 and the formal synthesis of unnatural (-)-lycopladine A [(-)-6] from (7S,7aS)-9.

Original languageEnglish
Pages (from-to)4522-4532
Number of pages11
JournalJournal of Organic Chemistry
Volume76
Issue number11
DOIs
Publication statusPublished - 2011 Jun 3

ASJC Scopus subject areas

  • Organic Chemistry

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