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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.