An Approach to Pseudomonic Acids from Acetylenic Precursors: Synthesis of 2-(Hydroxymethyl)-3-butyn-1-ol

Article abstract of DOI:10.1021/jo00364a003

The acetonide of 2-(hydroxymethyl)-3-butyn-1-ol (17) was prepared from bis(hydroxymethyl)malonate (11) or from 1,3-dihydroxypropanone (22).Alternative routes to 17 involving the intermediacy of highly unstable alkynal 21 or the corresponding acetate were unsuccessful.Condensation of the anion of 17 with aldehyde 30 followed by semihydrogenation and deprotection afforded keto triol 33, which cyclized stereoselectively to dihydropyran 34.Osmylation and functional group manipulation afforded 40 and 42, precursors to pseudomonic acid C (1).