Stepwise approach for sterically hindered Csp3-Csp3 bond formation by dehydrogenative: O -alkylation and Lewis acid-catalyzed [1,3]-rearrangement towards the arylalkylcyclopentane skeleton of sesquiterpenes

Ban Fujitani; Kengo Hanaya; Takeshi Sugai; Shuhei Higashibayashi

doi:10.1039/d0cc01017k

Stepwise approach for sterically hindered C_sp³-C_sp³ bond formation by dehydrogenative: O -alkylation and Lewis acid-catalyzed [1,3]-rearrangement towards the arylalkylcyclopentane skeleton of sesquiterpenes

Ban Fujitani, Kengo Hanaya, Takeshi Sugai, Shuhei Higashibayashi

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

A stepwise dehydrogenative cross-coupling method was developed for the formation of sterically hindered C_sp³-C_sp³ bonds. Intramolecular dehydrogenative O-alkylation of a β-ketoester by 2,3-dichloro-5,6-dicyano-p-benzoquinone to form an oxolane followed by Lewis acid-catalyzed [1,3]-rearrangement furnished the sesquiterpene arylmethylcyclopentane skeleton. The formal syntheses of herbertane-type β-herbertenol, cuparane-type enokipodins A and B were also achieved.

Original language	English
Pages (from-to)	3621-3624
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	25
DOIs	https://doi.org/10.1039/d0cc01017k
Publication status	Published - 2020 Mar 28

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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Stepwise approach for sterically hindered C_sp³-C_sp³ bond formation by dehydrogenative : O -alkylation and Lewis acid-catalyzed [1,3]-rearrangement towards the arylalkylcyclopentane skeleton of sesquiterpenes. / Fujitani, Ban; Hanaya, Kengo ; Sugai, Takeshi et al.

In: Chemical Communications, Vol. 56, No. 25, 28.03.2020, p. 3621-3624.

Research output: Contribution to journal › Article › peer-review

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