Total synthesis of (+/-)-hedychenone: trimethyldecalin terpene systems via stepwise allenoate diene cycloaddition |
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| Authors: | Jung Michael E Murakami Masayuki |
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| Institution: | Department of Chemistry and Biochemistry, University of California-Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095, USA. jung@chem.ucla.edu |
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| Abstract: | 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. reaction: see text] |
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