received in UK for publication 20 June 19'77) A simplified alkylation of the acyclic or alicyclic lithium 1,2-enediolates has been recently developed in our laboratory to provide a convenient synthetic method of ketones and oxoalkanenitriles, la,c which has been extended to a new synthesis of cis-jasmone. lb We present herein that the method has been applied with success to a facile synthesis of the oxoalkanolides (1 2 3),2a-e which --constitute the parent ring system of biologically active substances such as diplodialides or methymycin and so on. 0 The readily available 1,2-enediolate 5 la-c from 4 with 2 equiv. of methyllithium in monoglyme at -20" was subjected to alkylation with 3-bromo-1-propanol (THF/HMPA 1:4,rt,21hr) to give the cis-fused bicyclic glycol z3 [mp 86-87',ir max (nujo1)3300cm-1] in 46% yield. Oxidation of 2 (Pb(OAc)4/benzene,rt,2hr) afforded 5-ketooctanolide 1 [ir max(neat)1720,1700cm-1 ,ms 156(M+)] as a colorless oil in a nearly quantitative yield. The stereochemistry of the cis-glycol 2 was confirmed by conversion to the carbonate g3 [mp 29-30Β°, ir max(neat)l795cm-'1 ((COC1)2/Et3N/ CH2C12,rt,lhr). The reaction processes involved are demonstrated in Scheme 1.