SYNTHESIS OF PYRROLIZIDINES AND INDOLIZIDINES BY THE INTRAMOLECULAR CYCLOADDITION OF AZIDES WITH ELECTRON-RICH 1,3-DIENES - A SYNTHETIC EQUIVALENT OF A NITRENE DIENE CYCLOADDITION

被引:75
作者
PEARSON, WH [1 ]
BERGMEIER, SC [1 ]
DEGAN, S [1 ]
LIN, KC [1 ]
POON, YF [1 ]
SCHKERYANTZ, JM [1 ]
WILLIAMS, JP [1 ]
机构
[1] UNIV MICHIGAN,DEPT MED CHEM,ANN ARBOR,MI 48109
关键词
D O I
10.1021/jo00309a016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkyl azides were found to undergo intramolecular cycloadditions with certain 1,3-dienes to provide 2,3,5,7a-tetrahydro-1H-pyrrolizines and 3,5,6,7,8,8a-hexahydroindolizines in one operation (e.g., 12 →13 and 17 →18). The presence of an electron-donating group on the diene (sulfur, selenium, or oxygen) was required to avoid alternative rearrangement processes. The cyclization of chiral azidodienes proceeded with high diaster-eoselectivity to produce materials that are closely related to several alkaloidal natural products. New methods for the synthesis of the requisite heterosubstituted 1,3-dienes were developed. © 1990, American Chemical Society. All rights reserved.
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页码:5719 / 5738
页数:20
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