Photochemical access to tetra- and pentacyclic terpene-like products from R-(+)-sclareolide
Photochemical access to tetra- and pentacyclic terpene-like products from R-(+)-sclareolide
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DOI：
10.1021/jo034177y
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发表时间：
2003-08-22
影响因子：
3.6
通讯作者：
Sierra, MA
中科院分区：
文献类型：
--
作者：
de la Torre, MC;García, I;Sierra, MA
Fused tetracyclic oxetanes 4, highly substituted cyclobutenes 6, and the pentacyclic derivatives 7 and 8 were obtained by irradiation of derivatives 3 that were prepared from commercial R-(+)-sclareolide (1) in three steps. Compounds 4 are formed through a Paterno-Buchi reaction, while tricyclic derivatives 6 are the fragmentation products of the first formed oxetanes. In clear contrast, cyclopentenyl and 3-furyl derivatives, 3e and 3f, gave the [2+2] adducts, namely pentacyclic derivatives 7 and 8. All the reported reactions are totally regio- and stereoselective, with the exception of the cyclization of furyl derivative 3f, which gave the mixture of both the crossed (7b) and the right (8) isomers.
