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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.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

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.