Ieodomycin B와 Analogs의 효율적인 합성법

Abstract

Marine-derived microorganisms are increasingly recognized as the true metabolic sources of marinenatural products with therapeutic and pharmaceutical importance.Ieodomycin B is among the fourunsaturated fatty acids discovered from bioassay-guided isolation of the culture extract of a marine Bacillus sp. 09ID194 obtained from sediment in Ieodo, Republic of Koreas southern reef. As part of our on-going program for the discovery of bioactive substances from marine organisms and the subsequent construct of marine natural product-based small molecular library, it was an urgent need to develop an efficient synthesis of ieodomycins for material supply. Herein we describe the efficient syntheses of ieodomycin B and its analogs using (1) Ti-catalyzed asymmetric allylation of an aldehyde. (2) Stereoselective iodolactonization. (3) Completion of the synthesis of ieodomycin B and its analogs by coupling of various allyl tributyltin compounds with the corresponding iodolactone.say-guided isolation of the culture extract of a marine Bacillus sp. 09ID194 obtained from sediment in Ieodo, Republic of Koreas southern reef. As part of our on-going program for the discovery of bioactive substances from marine organisms and the subsequent construct of marine natural product-based small molecular library, it was an urgent need to develop an efficient synthesis of ieodomycins for material supply. Herein we describe the efficient syntheses of ieodomycin B and its analogs using (1) Ti-catalyzed asymmetric allylation of an aldehyde. (2) Stereoselective iodolactonization. (3) Completion of the synthesis of ieodomycin B and its analogs by coupling of various allyl tributyltin compounds with the corresponding iodolactone.