Studies Directed Toward the Total Synthesis of the Ezomycins, the Octosyl Acids and Related Antibiotics

Abstract

The ezomycins A, B and C, and the octosyl acids are nucleoside antibiotics endowed with an unprecedented structural feature, namely, a bicyclic trans-fused ring system which is part of a 3, 7-anhydrooctose structure. Methods were explored for the construction of such bicyclic rings. Trans-fused perhydrofuropyran models, bicyclic 2-deoxy-3, 7-anhydrooctosyl nucleosides and acyclic analogs related to the target molecules were synthesized by efficient regio- and stereocontrolled routes. Bicyclic lactones derived from carbohydrate precursors were also synthesized and their structures related to sesquiterpene α-methylene lactones. 0033-4545/81/0101-0129$02.00/0 © 1981, IUPAC. All rights reserved. © IUPAC