Elaboration of sclareol by Claisen rearrangement
Abstract
Transetherification of sclareol (labd-14-ene-8,13-diol)(1) with triethyl orthoacetate and subsequent rearrangement gave (E)- and (Z)-ethyl 8-hydroxylabd-13-en-15-ylacetate (2) and (3)(R = CO2Et). Products of cyclisation of these esters with tin(IV) chloride in benzene were characterised. Similar reactions with sclareol monoacetate (11) are described and stereochemical implications are discussed.