203. “The Synthesis of Boronolide”
     Jefford, C.W.; Moulin, M.-C.
     Helv. Chim. Acta 1991, 74, 336-342.

Racemic boronolide (1) is prepared in six steps in 4.4% overall yield from acrolein dimer 6 and 1-(trimethyl-silyl)hex-1-yne (8). The latter, by hydromagnesiation, is condensed with 6 to give the corresponding threo-allylic alcohol 13 (Scheme 2). Conversion of 13 to the erythro-allylic alcohol 5 (Scheme 3), bis-hydroxylation, and acetylation afford 1.

DOI : 10.1002/hlca.19910740213 

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