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Communication | Special issue | Vol 8, No. 1, 1977, pp.237-242
Published online, 1st January, 1970
DOI: 10.3987/S(S)-1977-01-0237
Selective Methyl and Methylene Migration in the Epoxy Derivatives Derived from 1-Abietic Acid

Masayuki Shimagaki,* Akira Anazawa, Takeshi Oishi, and the late Akira Tahara

*The Institute of Physical and Chemical Research, Wako-shi, Saitama 351-0198, Japan

Abstract

The α-epoxide (6) derived from l-abietic acid (1) caused a stereoselective methyl migration to its 13β-position giving, 8 in 54.2 % yield on BF3·Et2O treatment in benzene. On the other hand, the β-epoxide (7) gave rise to a methylene migration to give 9 or 10 in 63.5 % yield. The 13β-methyl derivative (8) was converted to isohibane (13).