✦ LIBER ✦

First total synthesis of a new sesquiterpenoid natural product, (±)-3-(2,4-dihydroxybenzoyl)-4,5-dimethyl-5-(4,8-dimethyl-3(E),7(E)-nonadien-1-yl)tetrahydro-2-furanone

✍ Scribed by Hidemi Yoda; Kazuhide Maruyama; Kunihiko Takabe

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 113 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00146-1

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✦ Synopsis

An efficient and stereodefined process is described for the first preparation of a new prenyl-benzoylfuranone type sesquiterpenoid, (±)-3-(2,4-dihydroxybenzoyl)-4,5-dimethyl-5-(4,8-dimethyl-3(E),7(E)-nonadien-1-yl)tetrahydro-2-furanone. The synthetic strategy is based on nucleophilic addition of organometallic reagents to the functionalized ketoamides elaborated from dihydroxyacetone dimer for the stereoselective construction of the key quaternary carbon center in the target compound.

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