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Communication | Special issue | Vol 79, No. 1, 2009, pp.403-410
Published online, 3rd December, 2008
DOI: 10.3987/COM-08-S(D)52
Total Synthesis and the Confirmation of the Revised Structures of Botcinins A and B

Hiroki Fukui, Keisuke Tsuji, Yuma Umezaki, and Isamu Shiina*

*Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan

Abstract

The stereoselective total syntheses of botcinins A (1) and B (2), and homobotcinin E (4), a homologue of botcinin E (3), have been achieved starting from a polyoxygenated tetrahydropyran intermediate 15 via formation of botcinic acid (12) and botcineric acid (13). Through the total syntheses, three actual relationships are revealed, that is, (i) the structure of botcinin A (1) is identical with the revised structure of the natural compound, which was formerly assumed to be 3-O-acetyl-2-epibotcinolide (5), (ii) the structure of botcinin B (2) is identical with the revised structure of the natural compound, which was supposed to be 3-O-acetyl-2-epihomobotcinolide (6), and (iii) the structure of the natural compound formerly assumed to be 2-epihomobotcinolide (8) must be revised to that of homobotcinin E (4).