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Paper | Special issue | Vol 99, No. 2, 2019, pp.1086-1094
Published online, 8th January, 2019
DOI: 10.3987/COM-18-S(F)74
Second-Generation Synthesis of a Chiral Building Block for Oxygenated Terpenoids via a Ring-Contractive Coupling with a Secondary Alcohol

Sayuri Saito, Hiroyuki Yamakoshi, and Seiichi Nakamura*

*Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan

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.