Studies Directed toward the Total Synthesis of Lactonamycin: Control of the Sense of Cycloaddition of a Quinone through Directed Intramolecular Catalysis | Zendy

Cox Christopher D. | Zendy; Siu Tony | Zendy; Danishefsky Samuel J. | Zendy

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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.

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