The synthesis and cationic cyclization of 2‐[6‐(3‐methoxyphenyl)‐2‐methyl‐(E)‐3‐hexenyl]‐3‐methyl‐2‐cyclopentenol (12) was investigated. The major cyclization products were 1‐ and 3‐methoxy‐11α,17‐dimethyl‐1,3,5(10),13(17)‐gonatetraene (14a and 15a) indicating a high degree of asymmetric induction by the pro‐C(11) chiral centre. Compound 15a was converted into DL‐11α‐methylestrone methyl ether (18).
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Groen et al. (1979) studied this question.
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