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Efficient and Chirally Specific Synthesis of Phenanthro‐Indolizidine Alkaloids by Parham‐Type Cycloacylation
Author(s) -
Wang Ziwen,
Li Zheng,
Wang Kailiang,
Wang Qingmin
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900920
Subject(s) - indolizidine , enantiopure drug , chemistry , modular design , stereochemistry , enantioselective synthesis , combinatorial chemistry , organic chemistry , alkaloid , computer science , catalysis , programming language
A concise, efficient and modular route involving Parham‐type cycloacylation as the key step has been used to synthesize six enantiopure phenanthro‐indolizidine alkaloids 1a – c . The preparation of enantiomerically pure tylophora alkaloids and their seco analogues on a large‐scale is now feasible. The alcohol intermediates 8a – c , which are difficult to prepare by other synthetic methodologies, have been synthesized by a metallation–cyclization–reduction sequence in excellent yields.