First total synthesis of (±)-methyl gummiferolate using a homoallyl-homoallyl radical rearrangement reaction

被引:22
作者
Toyota, M [1 ]
Yokota, M [1 ]
Ihara, M [1 ]
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1021/ol990264u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of (+/-)-methyl gummiferolate (Ib) has been achieved with a high diastereoselectivity. The key steps included the homoallyl-homoallyl radical rearrangement reaction of the enyne 8 to afford the suitably functionalized bicyclo[2.2.2]octane 9 and the intramolecular Diels-Alder reaction of the tetraene 12 for the construction of the AB ring system of Ib.
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页码:1627 / 1629
页数:3
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