Synthetic photochemistry. LXVII. A total synthesis of (±)-hinesol and (±)-agarospirol via retro-benzilic acid rearrangement

DOI: 10.1246/bcsj.68.2393

Source and publish data:

Bulletin of the Chemical Society of Japan p. 2393 - 2399 (1995)

Update date:2022-08-04

Topics:

Authors:

Hatsui Hatsui

Wang Wang

Takeshita

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Article abstract of DOI:10.1246/bcsj.68.2393

A mild base-catalyzed retro-benzilic acid rearrangement of a proto-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-dicarbonyl function and C₁-homologation furnished (±)-hinesol and (±)-agarospirol.

Full text of DOI:10.1246/bcsj.68.2393

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