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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Enantiospecific Semisynthesis of Puupehedione-Type Marine Natural Products
Hong-Shuang Wang1, Hui-Jing Li1, Xiang Nan1
1School of Marine Science and Technology, Harbin Institute of Technology , Weihai 264209, China.
Abstract:
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.

