Gram scale synthesis of the C(1)-C(9) fragment of amphidinolide C

TETRAHEDRON

卷:69

Article

Morra, Nicholas A.¹  Pagenkopf, Brian L.¹ 

[1] Univ Western Ontario, Dept Chem, London, ON N6A 5B7, Canada

关键词: Amphidinolide;    Aerobic oxidation;    Asymmetric dihydroxylation;    Hydrostannylation;    Natural products;   

DOI  :  10.1016/j.tet.2013.07.026

来源: Elsevier

【 摘 要 】

An allylic cis-epoxide prepared by Sharpless asymmetric epoxidation was transformed in nine steps and 41% overall yield to the cyclization precursor 4 via a key one carbon homologation. Cobalt-catalyzed aerobic oxidative cyclization of 4 gave the trans-THF in 94% yield at gram scale. Subsequent manipulations, including a Still-Gennari olefination, Sharpless asymmetric dihydroxylation, Corey-Fuchs alkynylation, and Kazmaier hydrostannylation provided the fully functionalized C(1)-C(9) fragment 2 suitable for cross-coupling. The sequence is readily scalable and provides gram quantities of 2. (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

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