3 years ago

Enantiospecific Semisynthesis of Puupehedione-Type Marine Natural Products

Enantiospecific Semisynthesis of Puupehedione-Type Marine Natural Products
Yuan-Yuan Luo, Hui-Jing Li, Hong-Shuang Wang, Xiang Nan, Yan-Chao Wu
An enantiospecific semisynthesis of puupehedione was achieved from sclareolide in only 7 steps with an overall yield of 25%. The key drimanal trimethoxystyrene skeleton was constructed by the palladium-catalyzed cross-coupling reaction of an aryl iodine and a drimanal hydrazone. An in situ CAN-oxidation/intramolecular oxa-Stork–Danheiser transposition tandem reaction was used as a powerful tool to install concurrently the C and D rings of puupehedione in a one-pot fashion. Its applicability was also showcased by the semisynthesis of puupehenone and puupehenol.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02413

DOI: 10.1021/acs.joc.7b02413

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