Towards a [4+2] Route to (+/-)-decarestrictines J and H: Synthesis of a Bicyclic Key-intermediate

Abstract

International audienceTowards a [4+2] Route to ()-decarestrictines J and Towards a [4+2] Route to ()-decarestrictines J and Towards a [4+2] Route to ()-decarestrictines J and Towards a [4+2] Route to ()-decarestrictines J and Towards a [4+2] Route to ()-decarestrictines J and Sopa Chewchanwuttiwong [a], Arnaud Martel [b], Duang Buddhasukh [a], Eric Brown [b], Sopa Chewchanwuttiwong [a], Arnaud Martel [b], Duang Buddhasukh [a], Eric Brown [b], Sopa Chewchanwuttiwong [a], Arnaud Martel [b], Duang Buddhasukh [a], Eric Brown [b], Sopa Chewchanwuttiwong [a], Arnaud Martel [b], Duang Buddhasukh [a], Eric Brown [b], Sopa Chewchanwuttiwong [a], Arnaud We describe here the development of an approach to the synthesis of 3-oxo-7-hydroxy-9-decanolides of biological interest. This strategy involves two key steps : the inverse electron demand Hetero-Diels-Alder reaction of an original dienophile (1,5-dimethoxy-cyclohexa-1,4-diene), which will ensure the construction of an advanced structure in a very short number of steps, and the ring opening of a functionalized bicyclic lactol, leading to the requisite decanolide. The diastereocontrolled synthesis of such a lactol will be detailed in this communication