Asymmetric Total Synthesis of Norzoanthamine

Autor:	Haibing He, Xiao-Li Zhao, Zhengyuan Xin, Shuanhu Gao, Hui Wang
Rok vydání:	2021
Předmět:	Olefin fiber 010405 organic chemistry Stereochemistry Radical Acetal Total synthesis Zoanthamine General Chemistry General Medicine 010402 general chemistry 01 natural sciences Radical cyclization Catalysis 0104 chemical sciences Stereocenter chemistry.chemical_compound Norzoanthamine chemistry
Zdroj:	Angewandte Chemie. 133:12917-12922
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.202102643
Popis:	We report herein the asymmetric total synthesis of norzoanthamine using radical reactions as key steps for rapid access to the congested carbocyclic core, which is the major synthetic challenge for most zoanthamine alkaloids. (1) The Ueno-Stork radical cyclization was applied to construct the adjacent quaternary centers at the C-9 and C-22 positions; (2) a Co-catalyzed HAT radical reaction was successfully applied to construct the quaternary center at C-12 via Csp3 -Csp2 bond formation; (3) a Mn-catalyzed HAT radical reaction was used to stereospecifically reduce the tetra-substituted olefin (C13=C18) and install the contiguous stereocenters in proximity to the quaternary center. A one-pot bio-inspired cyclization step was finally applied to forge the unstable bis-amino acetal skeleton. Our approach can precisely control the stereochemistry of seven vicinal stereocenters and effectively construct the highly congested heptacyclic skeleton.
Databáze:	OpenAIRE
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