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Total Synthesis of (±)-Hedychenone:  Trimethyldecalin Terpene Systems via Stepwise Allenoate Diene Cycloaddition

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journal contribution
posted on 07.12.2006, 00:00 by Michael E. Jung, Masayuki Murakami
The total synthesis of hedychenone 1 is described. The cycloaddition of the hindered diene 2 and the allenecarboxylate 3 has been shown conclusively to proceed via the [2+2] cycloadduct 5 to give a 2:1 mixture of the desired formal Diels−Alder adducts, the exo and endo isomers 4xn and is thus a stepwise [4+2] cycloaddition. The exo isomer 4x was converted in four steps (reduction, oxidation, olefination, and desilylation) into hedychenone 1.