6-epi-Ieodomycin B와 Analogs의 효율적인 합성법

Abstract

In our research program aiming to understand the chemical diversity of marine biological resources, four new antimicrobial fatty acids, ieodomycins A-D were discovered from bioassay-guided isolation of the culture extract of a marine Bacillus sp. 09ID194 from sediment in Ieodo, Rupublic of Korea’s southern reef. Due to the structural uniqueness and the biological activities (antimicrobial activities), we initiated the synthetic study of ieodomycins. In this presentation, the efficient synthesis of 6-epi-ieodomycin and its analogs will be described.The efficient syntheses of 6-epi-ieodomycin B and its analogs are described in this presentation. Our synthesis features (1) Ti-catalyzed asymmetric allylation of an aldehyde. (2) Stereoselective iodolactonization. (3) The Lewis Acid catalyzed Allylation of ketone with potassium allyltrifluoroborate. (4) Dehydration of allylic alcohol with Burgess reagent.us sp. 09ID194 from sediment in Ieodo, Rupublic of Korea’s southern reef. Due to the structural uniqueness and the biological activities (antimicrobial activities), we initiated the synthetic study of ieodomycins. In this presentation, the efficient synthesis of 6-epi-ieodomycin and its analogs will be described.The efficient syntheses of 6-epi-ieodomycin B and its analogs are described in this presentation. Our synthesis features (1) Ti-catalyzed asymmetric allylation of an aldehyde. (2) Stereoselective iodolactonization. (3) The Lewis Acid catalyzed Allylation of ketone with potassium allyltrifluoroborate. (4) Dehydration of allylic alcohol with Burgess reagent.