The Journal of Organic Chemistry

Quassinoids. An approach to the BCDE rings of bruceantin

RV Stevens, AP Vinogradoff

文献索引：Stevens, Robert V.; Vinogradoff, Anna P. Journal of Organic Chemistry, 1985 , vol. 50, # 21 p. 4056 - 4062

全文：HTML全文

被引用次数: 13

摘要

Synthesis of a model 28 for the BCDE rings of bruceantin via a BC-BCE-BCED ring strategy is presented. The sequence includes Diels-Alder reaction of methyl 3J-hexadienoate 9 and quinone 8 derived from o-vanillyl alcohol, selenocyclization of hydroxy diester 22, and lactone formation to give the BCDE system 25. Manipulation on 25 showed the viability of its functional groups for further development in the synthetic strategy.