Carbasugar Synthesis via Vinylogous Ketal: Total Syntheses of (+)-MK7607, (-)-MK7607, (-)-Gabosine A, (-)-Epoxydine B, (-)-Epoxydine C, epi-(+)-Gabosine E and epi-(+)-MK7607.

Abstract

Carbasugars, the carbocyclic analogues of sugars, constitute an important class of natural products with more than 140 members known and have attracted much attention due to their diverse biological activities like anticancer, antibacterial, herbicidal, and various enzyme inhibitory activities. As many carbohydrates are involved in various cellular signaling pathways, there is great interest in synthesis and biological exploration of carbasugars. Herein, we have developed a methodology to install an α,β-unsaturated aldehyde functionality on different inositols and derivatives by vinylogous elimination of the O-protecting group under mildly acidic condition. We have illustrated the versatility and utility of our methodology by the total syntheses of seven carbasugars viz. (-)-MK7607, (-)-gabosine A, (-)-epoxydine B, (-)-epoxydine C, (+)-MK7607, 1-epi-(+)-MK7607 and 1-epi-(+)-gabosine E.