Tandem manganese(III)-based oxidative free-radical cyclizations terminated by addition to furans. Formal synthesis of 15-acetoxypallescensin-A

被引:13
作者
Snider, BB [1 ]
O'Hare, SM [1 ]
机构
[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1081/SCC-100108225
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of beta -keto ester 12 with 2 equiv. of Mn(OAc)(3). 2H(2)O in KOAc-buffered MeOH followed by acidic workup afforded 51 % of tricyclic furan 14 indicating that oxidative cyclizations can be terminated by addition to furans. Reduction of 14 with LAH provided 7, completing a five-step formal synthesis of 15-acetoxypallescensin-A.
引用
收藏
页码:3753 / 3758
页数:6
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