Syntheses of (+)-exo-, (+)-endo-Brevicomin, and (-)-Frontalin via Enzymatic Reactions

Jun Ichi Ishiyama, Manabu Toi, Chiaki Ichikawa, Shuichi Oi, Yoshio Inoue

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

(+)-exo-Brevicomin of enantiomerically pure form and its (+)-endo-isomev of 77% e. e. were synthesized via lipase-eatalyzed acetylation of syn-2-(l-hydroxypropyl)-6-methyl-3,4-dihydro-2 H-pyran (syn-2) and anti-2, respectively, both of which were accessible by stereoselective reduction of 2-propionyl-6-methyl-3, 4-dihydro-2 H-pyran (1). Similarly, (-)-forntalin of 91% e. e. was obtained via consecutive enzymatic hydrolysis or acetylation of 2-methoxycarbonyl (5), 2-hydroxymethyl (6), and 2-acetoxymethyl derivative (7) of 2, 6-dimethyl-3, 4-dihydro-2 H-pyran.

Original languageEnglish
Pages (from-to)1162-1166
Number of pages5
JournalNIPPON KAGAKU KAISHI
Volume1993
Issue number10
DOIs
Publication statusPublished - 1993

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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