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New Lead Structures by Diels‐Alder Reactions of Streptazolin with Naphthoquinones
Author(s) -
Grabley Susanne,
Kluge Heinz,
Hoppe HansUllrich
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198706641
Subject(s) - selectivity , chemistry , cycloaddition , diene , diels–alder reaction , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , natural rubber
Striking antibiotic and cytotoxic properties are exhibited by the products 3 and derivatives thereof. Compounds 3 are obtained in good yields from the chiral diene streptazolin 1 (R 3 H) and naphthoquinones 2 . The low endo‐/exo ‐selectivity and diastereofacial selectivity of the cycloaddition are, by way of exception, an advantage; they make a number of isomers accessible for the screening of natural products. (R 1 , R 2 H, OH, OAc; R 3 H, Ac, SiMe 2 t Bu.)