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Synthesis and Conformational Analysis of Geodiamolide Analogues
Author(s) -
Marimganti Srinivasa,
Wieneke Ralph,
Geyer Armin,
Maier Martin E.
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700024
Subject(s) - chemistry , ring (chemistry) , ring size , stereochemistry , molecular dynamics , nuclear magnetic resonance spectroscopy , computational chemistry , organic chemistry
Abstract Starting with the ω‐hydroxy and ω‐amino acid derivatives 13 and 21 , the two closely related geodiamolide analogs 32 and 35 , respectively, were prepared. Compared to the natural cyclodepsipeptide geodiamolide ( 1 ), the macrocycles 32 and 35 have a smaller ring size (17‐ vs. 18‐membered). Conformational analysis by ROESY spectroscopy and molecular dynamics simulation revealed that the reduced ring size causes the polypropionate sector to flip with regard to the geodiamolide conformation.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)