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High‐Yielding Enantioselective Synthesis of the Macrolactam Aglycon of Sch 38516 from Two Units of (2 R )‐2‐Ethyl‐4‐penten‐1‐ol
Author(s) -
Martín Manuel,
Mas Gemma,
Urpí Fèlix,
Vilarrasa Jaume
Publication year - 1999
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/(sici)1521-3773(19991018)38:20<3086::aid-anie3086>3.0.co;2-d
Subject(s) - enantioselective synthesis , stereochemistry , chemistry , organic chemistry , catalysis
The same precursor —namely, (2 R )‐2‐ethyl‐4‐penten‐1‐ol—was used to obtain fragments C9–C13 and C1–C8 of 1 , the aglycon of Sch 38516 (which is active against Candida sp.) and fluvirucin B 1 (which is active against influenza A virus). The key steps of the synthesis were the aldol‐like reaction between the two fragments and the macrolactamization of a 13‐azidotridecanoic acid derivative (see scheme). MOM=methoxymethyl, Py=2‐pyridyl.