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

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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†

Ban Fujitani,^a Kengo Hanaya,^a Takeshi Sugai

^a and Shuhei Higashibayashi

*^a

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* Corresponding authors

^a Department of Pharmaceutical Sciences, Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan
E-mail: higashibayashi-sh@pha.keio.ac.jp

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.

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Article information

DOI: https://doi.org/10.1039/D0CC01017K
Article type: Communication
Submitted: 08 Feb 2020
Accepted: 20 Feb 2020
First published: 27 Feb 2020

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Chem. Commun., 2020,56, 3621-3624

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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

B. Fujitani, K. Hanaya, T. Sugai and S. Higashibayashi, Chem. Commun., 2020, 56, 3621 DOI: 10.1039/D0CC01017K

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Chemical Communications