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Studies towards an Enantioselective Total Synthesis of Sarain A: A Concise Asymmetric Construction of the Diazatricyclic Core
Author(s) -
Yang RuiFeng,
Huang PeiQiang
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001582
Subject(s) - enantioselective synthesis , core (optical fiber) , computer science , intramolecular force , block (permutation group theory) , tandem , michael reaction , ring (chemistry) , combinatorial chemistry , chemistry , stereochemistry , mathematics , organic chemistry , combinatorics , engineering , catalysis , telecommunications , aerospace engineering
A powerful chiral building block : A concise enantioselective synthesis of the diazatricyclic core of sarain A has been accomplished. The novel strategy relies upon the versatile chiral building block ( R )‐ 1 (see scheme), and features a tandem Horner–Wadsworth–Emmons–aza‐Michael reaction, an intramolecular Michael reaction, and the diastereoconvergent formation of the third ring. Diazatricyclic core 2 possesses all of the necessary functionality for further elaboration into sarain A.
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