Total synthesis of (-)-4-desacetoxy-1-oxovindoline: Single atom exchange of an embedded core heteroatom in vindoline

TETRAHEDRON

卷:87

Article

Boon, Byron A.^1,2  Yu, Yi-Yun^1,2  Boger, Dale L.^1,2 

[1] Scripps Res Inst, Dept Chem, 10550 N Torrey Pines Rd, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, 10550 N Torrey Pines Rd, La Jolla, CA 92037 USA

关键词: Oxadiazole cycloaddition cascade;    Vindoline analogue;    Vinca alkaloids;   

DOI  :  10.1016/j.tet.2021.132117

来源: Elsevier

【 摘 要 】

A concise total synthesis of (-)-4-desacetoxy-1-oxovindoline is disclosed, bearing a single heteroatom exchange in the core structure of the natural product 4-desacetoxyvindoline. Central to the synthesis is powerful oxadiazole intramolecular [4 + 2]/[3 + 2] cycloaddition cascade that formed four C-C bonds, created three new rings, and established five contiguous stereocenters about the new formed central 6-membered ring. (C) 2021 Elsevier Ltd. All rights reserved.

【 授权许可】

Free