Concise synthesis and transannular inverse electron demand Diels-Alder reaction of [3](3,6)pyridazino[3](1,3)indolophane. Rapid access to a pentacyclic indoloid system

被引:57
作者
Bodwell, GJ [1 ]
Li, J [1 ]
机构
[1] Mem Univ Newfoundland, Dept Chem, St John, NF A1B 3X7, Canada
关键词
D O I
10.1021/ol017014+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
GRAPHICS The title compound was synthesized concisely from indole. A 2-fold sequential hydroboration/Suzuki-Miyaura cross-coupling was employed to generate the cyclophane. When heated in N,N-diethylaniline, it underwent a transannular inverse electron demand Diels-Alder (IEDDA) reaction to form a pentacyclic product, which appears to be well suited as a precursor to a variety of indole alkaloids such as strychnine.
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页码:127 / 130
页数:4
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