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Synlett 1995; 1995(1): 35-37
DOI: 10.1055/s-1995-4880
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A Short Synthesis of Hinesol and Agarospirol via Photochemical Construction of Vetispirane Framework Based on the retro-Benzilic Acid Rearrangement

Toshihide Hatsui, Jin-Jun Wang, Shin-ya Ikeda, Hitoshi Takeshita*
  • *Institute of Advanced Material Study, 86, Kyushu University, Kasuga-koen, Kasuga, Fukuoka 816, Japan
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Publication Date:
31 December 2000 (online)

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A mild base-catalyzed retro-benzilic acid rearrangement of a proto-[2+2] photocycloadduct, formed in highly stereoselective photoaddition of methyl 2,4-dioxopentanoate to 1,5-dimethyl-6-methylene-1-cyclohexene, afforded a spiro[4.5]decenedione derivative. Reductive elimination of the α-diketone function and C1-homologation furnished (±)-hinesol and (±)-agarospirol.

retro-Benzilic acid rearrangement - hinesol - hinesene - agarospirol