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- Title
Multiple Wagner-Meerwein Shift. Biogenesis-like conversion of (±)-Δ<sup>7,8</sup>-Protoilludene to (±)-Hirsutene and related reactions.
- Authors
Hayano, Kiyoharu; Ohfune, Yasufumi; Shirahama, Haruhisa; Matsumoto, Takeshi
- Abstract
Experimental details are given for the previous preliminary reports concerning conversion of protoilludane ( 28) to hirsutene ( 3) and related reactions. Treatment of each of the bicyclic analogs 9, 10, 12 and 13 of the former compound afforded a hirsutene analog 8, through multiple 1,2-shift, together with other products. Treatment of a mixture of α- and β-protoilludene -epoxides ( 29α and 29β) with BF3 · Et2O in hexane yielded hirsutane derivatives 30 and 32. Compound 30 in turn was converted to endo-hirsutene 36, which had already been isomerized to hirsutene ( 3).
- Publication
Helvetica Chimica Acta, 1981, Vol 64, Issue 5, p1347
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19810640511