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Absolute stereochemistry of the strevertenes
Author(s) -
Guo Jinsong,
Schlingmann Gerhard,
Carter Guy T.,
Nakanishi Koji,
Berova Nina
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:1<43::aid-chir8>3.0.co;2-n
Subject(s) - chemistry , stereocenter , chirality (physics) , stereochemistry , absolute configuration , antifungal , absolute (philosophy) , chromophore , cotton effect , enantioselective synthesis , circular dichroism , organic chemistry , chiral symmetry , catalysis , medicine , philosophy , physics , quantum mechanics , dermatology , quark , nambu–jona lasinio model , epistemology
The CD exciton chirality method was applied to determine the absolute stereochemistry of the strevertenes, antifungal pentaene macrolides produced by Streptoverticillium sp. LL‐30F848. The CD difference spectrum of strevertene A methyl ester 15‐dimethylaminobenzoate showed a positive couplet between the dimethylaminobenzoate and the pentaene chromophores, and therefore established the 15 R configuration. Thus, by considering the relative configurations of the remaining stereogenic centers as derived from X‐ray crystallography and ROESY experiments, the absolute stereochemistry of the strevertenes is established as 2R, 3S, 5S, 7S, 11R, 13R, 14R, 15R, 26S and 27R . Chirality 12:43–51, 2000. © 2000 Wiley‐Liss, Inc.