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The Total Synthesis of Heliquinomycinone
Author(s) -
Siu Tony,
Qin Donghui,
Danishefsky Samuel J.
Publication year - 2001
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(20011217)40:24<4713::aid-anie4713>3.0.co;2-n
Subject(s) - regioselectivity , dihydroxylation , total synthesis , aldehyde , combinatorial chemistry , mitsunobu reaction , chemistry , stereochemistry , organic chemistry , enantioselective synthesis , catalysis
A strategy for the synthesis of heliquinomycin , a selective helicase inhibitor, hinges on the spirocyclization of precursor 3 . Naphthofuran 1 and aldehyde 2 were readily prepared and used in the synthesis of 3 . The key steps in the total synthesis of heliquinomycinone ( 4 ) include the regioselective dihydroxylation of 3 , and a novel spirocyclization under Mitsunobu conditions.