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《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2017,129(36):11030-11033
The first total synthesis of the tetracyclic sesquiterpenoid (+)‐dendrowardol C is described. It relies on an intramolecular aldol reaction to forge the central bicyclic scaffold and subsequent cyclobutane formation by cyclization of a γ‐triflyloxy ketone. Key is the treatment of the latter with lithium naphthalenide. Finally, the diastereoselective hydroboration of a 1,1‐disubstituted double bond is enabled by a chiral CoI catalyst. 相似文献
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Dong-Xing Tan Jie Zhou Chao-You Liu Dr. Fu-She Han 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(10):3862-3867
We present the first asymmetric total synthesis and absolute configuration determination of (+)-tronocarpine. The [6.5.7.6.6] pentacyclic core was constructed at an early stage by using a sequential cyclization strategy through a newly developed catalytic asymmetric Michael/aldol cascade to build the aza[3.3.1]-bridged cycle and a tandem reduction/hemiamidation procedure to assemble the seven-membered lactam. The side-chain functionalities were incorporated at a late stage by several appropriately orchestrated manipulations under mild conditions. The synthesis of enantiomerically pure (+)-tronocarpine was achieved through a 20-step longest linear sequence from tryptamine. 相似文献