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Studies in the Total Synthesis of Heliquinomycinone: Proof of Concept and Assembly of a Fully Mature Spirocyclization Precursor
Author(s) -
Qin Donghui,
Ren Rex X.,
Siu Tony,
Zheng Changsheng,
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<4709::aid-anie4709>3.0.co;2-q
Subject(s) - regioselectivity , dihydroxylation , aldehyde , total synthesis , combinatorial chemistry , chemistry , computer science , 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.