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A Short Synthesis of (±)‐13‐Deoxyserratine
Author(s) -
Cassayre Jérome,
Gagosz Fabien,
Zard Samir Z.
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020517)41:10<1783::aid-anie1783>3.0.co;2-i
Subject(s) - stereoselectivity , intramolecular force , yield (engineering) , total synthesis , cascade , chemistry , radical cyclization , alkaloid , stereochemistry , combinatorial chemistry , organic chemistry , materials science , chromatography , catalysis , metallurgy
A short and efficient total synthesis of (±)‐13‐deoxyserratine ( 3 ) features a highly stereoselective intramolecular Pauson–Khand reaction of 1 and a cascade of radical cyclizations starting with the amidyl radical 2 . The desired alkaloid 3 was thus obtained in ten steps in an overall yield of 12 %. THP=tetrahydropyranyl, TBS= tert ‐butyldimethylsilyl.