Second-generation synthesis of a chiral building block for oxygenated terpenoids via a ring-contractive coupling with a secondary alcohol

Sayuri Saito, Hiroyuki Yamakoshi, Seiichi Nakamura

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A much improved second-generation synthesis of a chiral building block, developed for the syntheses of C17-oxygenated steroids/triterpenoids and C9-oxygenated labdane diterpenoids, was accomplished by exploiting a ring-contractive coupling between an α-bromo-δ-valerolactone and (R)-seudenol, wherein the use of t-BuOK as a base allowed clean conversion to the corresponding tetrahydrofuran-2-carboxylate even with a small excess of the alcohol component.

Original languageEnglish
Pages (from-to)1086-1094
Number of pages9
JournalHeterocycles
Volume99
Issue number2
DOIs
Publication statusPublished - 2019
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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