Studies toward the total synthesis of clavulactone

被引：18
|
作者：
Zhu, Q
Qiao, LX
Wu, YK
Wu, YL
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 08期
关键词：
D O I：
10.1021/jo005683f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Synthetic studies directed toward a total synthesis of clavulactone are reported. In light of the analysis made in our previous work, cyclopentane 4a (a key intermediate in the present work) was synthesized through a radical-mediated ring closure of a rationally designed substrate 25. Using HWE reactions, the lower and upper side-chains of 4a were converted into an allyl chloride and an allyl cyanohydrin, respectively. Subsequent treatment of the allyl chloride/cyanohydrin in a highly diluted THF solution with sodium bis(trimethylsiliyl)amide led to intramolecular alkylation and thus completed a major endeavor in synthesizing the dolabellane framework, construction of the eleven-membered ring. SmI2-mediated lactonization as a model reaction for the formation of the alpha,beta -unsaturated delta -lactone segment of clavulactone is also described.
引用
收藏
页码：2692 / 2699
页数：8
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