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Total Synthesis of Stemarene and Betaerene Diterpenoids:Divergent Ring-Formation Strategy and Late-Stage C–H Functionalization

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摘要 A unified protecting group-free approach to two stemarene and two betaerene diterpenoids through a bioinspired two-phase strategy has been developed,and three of them were obtained for the first time via chemical synthesis.Starting from a common intermediate,two distinct tetracyclic frameworks containing diastereoisomeric bridged bicycles were constructed by a divergent ring reorganization strategy.Late-stage C–H functionalization through a xanthylation-oxygenation protocol furnished the corresponding oxygenated stereocenters or oxo functionality in high regio-and diastereoselective fashion within a complex hydrocarbon system.The stereochemical puzzles in(–)-2-acetoxybetaer13(17)-ene and(+)-7-acetoxybetaer-13(17)-ene were first predicted by the comparison of density functional theory(DFT)-nuclear magnetic resonance(NMR)data with the reported data and then unambiguously addressed through the total syntheses of natural products and three diastereomers.
出处 《CCS Chemistry》 CAS 2022年第3期987-995,共9页 中国化学会会刊(英文)
基金 Financial support from the National Natural Science Foundation of China(nos.22071205,21772164,and 21572187) NFFTBS(no.J1310024),and PCSIRT is acknowledged.
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