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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Total Synthesis of (-)-Ceforalide B and (-)-Cephanolides B-D
Zhongliu Sun1, Xin Fan1, Zezhong Sun1
1Department of Chemistry & Material Science, Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministryof Education of China, Northwest University, Xi'an 710127, China.
Abstract:
(-)-Ceforalide B (1) and (-)-cephanolides B-D (2-4) are benzenoid cephanolide diterpenoids possessing the same pentacyclic skeleton, which contains three C13-C15 substituent patterns and different benzylic oxidation states. An olefination/6π-electrocyclization/oxidative aromatization cascade has been verified as divergent access to three C13-C15 patterns. The benzylic aerobic oxidations enabled by the Co(OAc)2·4H2O/bromide salt/O2/PPh3/N-hydroxyphthalimide system have been developed to deliver expected site-selectivity and different oxidation states. Through the divergent strategy, total synthesis of (-)-ceforalide B and (-)-cephanolides B-D is accomplished.
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