Convenient synthesis of alcohol O-hemiesters using isopropenyl esters as acylating reagents: synthesis of hydrophilic oxaunomycin 10-O-hemiester derivatives

Abstract

Various types of alcohol O-hemiesters 7a–m were synthesized conveniently in good yield by reaction with isopropenyl esters 4a–f in the presence of a catalytic amount of conc. H₂SO₄ or toluene-p-sulfonic acid followed by selective deprotection of the terminal esters. This method was applied to a preparation of hydrophilic oxaunomycin 10-O-hemiester derivatives 14a, b and 19a–c.