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A short, formal, biomimetic synthesis of (+/-)-polygalolides A and B.

[reaction: see text] Reaction of bisacetoxy pyranone 9 with Et3N gave 3-oxidopyrylium ylide 10, which underwent a stereo- and regiospecific [5 + 2] cycloaddition with alpha-methylenebutyrolactone to afford 16 (34%). Treatment of 16 with Cs2CO3 resulted in hydrolysis of the lactone and acetate and conjugate addition of the hydroxyethyl group to the enone. Lactonization on acidification afforded 4 (57%), completing a two-step, formal synthesis of polygalolides A and B.[1]


  1. A short, formal, biomimetic synthesis of (+/-)-polygalolides A and B. Snider, B.B., Wu, X., Nakamura, S., Hashimoto, S. Org. Lett. (2007) [Pubmed]
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