Synthetic Studies of an 18-Membered Antitumor Macrolide, Tedanolide. 6. Synthesis of a Key Intermediate via a Highly Efficient Macrolactonization of Computer-Aid Designed Seco-Acid

Tomohiro MATSUSHIMA; Noriyuki NAKAJIMA; Bao-Zhong ZHENG; Osamu YONEMITSU

doi:10.1248/cpb.48.855

Tomohiro MATSUSHIMA, Noriyuki NAKAJIMA, Bao-Zhong ZHENG, Osamu YONEMITSU

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Keywords: macrolide, 18-membered lactone, macrolactonization, seco-acid, aldol reaction, calculation

JOURNAL FREE ACCESS

2000 Volume 48 Issue 6 Pages 855-860

DOI https://doi.org/10.1248/cpb.48.855

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Abstract

A stereoselective synthesis is described of the 18-membered lactone (2) via an efficient macrolactonization of the conformation-controlled seco-acid (3); this was designed with the aid of molecular mechanics (MM)-calculation and synthesized by coupling between the C1-C12 (4) and C13-C23 (5) fragments.

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