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Studies Directed toward the Total Synthesis of Lactonamycin: Control of the Sense of Cycloaddition of a Quinone through Directed Intramolecular Catalysis
Author(s) -
Cox Christopher D.,
Siu Tony,
Danishefsky Samuel J.
Publication year - 2003
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/anie.200352591
Subject(s) - regioselectivity , intramolecular force , cycloaddition , quinone , ring (chemistry) , chemistry , total synthesis , catalysis , stereochemistry , base (topology) , organic chemistry , mathematics , mathematical analysis
The rapid assembly of the ABCD tetracyclic ring system of lactonamycin involved the strong‐base‐induced regioselective Diels–Alder reaction of 1 and 2 to form advanced precursor 3 . Regiochemical control results from the suitably positioned hydroxy group, and thus only the desired isomer of 3 is obtained.