Constructing the architecturally distinctive ABD-tricycle of phomactin A through an intramolecular oxa-[3+3] annulation strategy

TETRAHEDRON

卷:67

Article

Buchanan, Grant S.²  Cole, Kevin P.¹  Li, Gang²  Tang, Yu³  You, Ling-Feng²  Hsung, Richard P.² 

[1] Eli Lilly & Co, Chem Prod R&D, Indianapolis, IN 46284 USA

[2] Univ Wisconsin, Div Pharmaceut Sci, Madison, WI 53705 USA

[3] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China

关键词: Phomactin A;    ABD-tricycle;    Intramolecular oxa-[3+3] annulation;    Atropisomers;    Rawal's Diels-Alder cycloaddition;   

DOI  :  10.1016/j.tet.2011.09.111

来源: Elsevier

【 摘 要 】

Our efforts in constructing the ABD-ring of phomactin A through an intramolecular oxa-[3+3] annulation strategy is described. This struggle entailed finding a practical and efficient preparation of annulation precursor, and a realization of the unexpected competing regioisomeric pathway. The success entailed accessing the A-ring through Diels Alder cycloaddition of Rawal's diene. Furthermore, the discovery that the regioisomers from the annulation existed as atropisomers with respect to the D-ring olefin and that they could be equilibrated to the desired ABD-tricycle, allowing large quantities of tricycle to be accessed. Published by Elsevier Ltd.

【 授权许可】

Free