A Diels–Alder Macrocyclization Enables an Efficient Asymmetric Synthesis of the Antibacterial Natural Product Abyssomicin C | Zendy

Zapf Christoph W. | Zendy; Harrison Bryce A. | Zendy; Drahl Carmen | Zendy; Sorensen Erik J. | Zendy

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A Diels–Alder Macrocyclization Enables an Efficient Asymmetric Synthesis of the Antibacterial Natural Product Abyssomicin C

Author(s) -

Zapf Christoph W.,

Harrison Bryce A.,

Drahl Carmen,

Sorensen Erik J.

Publication year - 2005

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.200502119

Subject(s) - natural product , diels–alder reaction , product (mathematics) , chemistry , alder , antibacterial activity , combinatorial chemistry , stereochemistry , organic chemistry , mathematics , biology , bacteria , catalysis , botany , geometry , genetics

An efficient and highly diastereoselective intramolecular Diels–Alder reaction is the basis of a concise asymmetric synthesis of the potent antibacterial natural product abyssomicin C (see formula). The complexity of the target structure was reduced to three fragments and required two carbonyl addition reactions to achieve key bond formations.

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