Abstract
AbstractThe total synthesis of the norsesquiterpene 7‐demethyl‐2‐methoxycalamenene (1) by a newly developed enantioselective silane‐terminated Heck reaction is described. The Pd0‐catalyzed transformation of the allylsilane 7, obtained from 3‐(3‐methoxyphenyl)propanol (2) in 7 steps, provides the tetralin 8 in 91% yield and with 92% ee in the presence of (R)‐BINAP. Transformation of 8 via 14 and 15 gives 1. The absolute configuration of 1 which has previously not been known was deduced from a single‐crystal X‐ray analysis of 10, obtained from the cyclization product 8 by hydroboration and acylation with camphanic acid chloride.
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