Photochemical rearrangements of highly functionalized longipinene derivatives

被引：10
|
作者：
JosephNathan, P [1 ]
MelendezRodriguez, M [1 ]
CerdaGarciaRojas, CM [1 ]
Catalan, CAN [1 ]
机构：
[1] UNIV NACL TUCUMAN,FAC BIOQUIM QUIM & FARM,INST QUIM ORGAN,RA-4000 S MIGUEL TUCUMAN,TUCUMAN,ARGENTINA
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 45期
关键词：
D O I：
10.1016/0040-4039(96)01848-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ultraviolet irradiation of 7 beta,9 alpha-diacetyloxylongipin-2-en-1-one (3) affords the vulgarone A derivative 5 and compound 7 which possesses a novel tricyclic sesquiterpene skeleton named pingilonane. The photorearrangements of 3 occur via [1,3] sigmatropic shifts of the C-4-C-10 or of the C-4-C-5 bond, respectively. Similarly, irradiation of 7 beta,8 alpha,9 alpha-triacetyloxylongipin-2-en-1-one (4) affords 6 and 8. Some biogenetic implications of these transformations are discussed. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：8093 / 8096
页数：4
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