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Stereocontrol in Pinacol Ring‐Contraction of Cyclopeptidyl Glycols: The Diazonamide C 10 Problem
Author(s) -
Chen Xin,
Esser Lothar,
Harran Patrick G.
Publication year - 2000
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(20000303)39:5<937::aid-anie937>3.0.co;2-a
Subject(s) - stereochemistry , contraction (grammar) , chemistry , metabolite , pinacol , ring (chemistry) , organic chemistry , biochemistry , biology , catalysis , endocrinology
Diazonamide A is a bioactive secondary metabolite whose synthesis and mode of action remain elusive a decade after its discovery. In this synthesis of the A/E/F‐ring fragment of the diazonamides, 1 was converted into a single isomer of 2 by a ring‐contraction rearrangement. The stereochemistry at C10 in 2 can be reliably predicted from the configuration of glycol 1 .