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Synlett 2021; 32(06): 605-610
DOI: 10.1055/s-0040-1705974
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Scandium Triflate Catalyzed Nazarov Cyclization of Arylvinyl Epoxides Derived from Alkoxides and Chloro(aryl)carbenes: A Facile Access to Resveratrol-Derived Natural Products

Nagam Satish
a   Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India   Email: gsudhakar@iict.res.in
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, UP, India
,
Gangarajula Sudhakar  ∗
a   Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India   Email: gsudhakar@iict.res.in
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, UP, India
› Author AffiliationsWe are grateful to the Science and Engineering Research Board, Department of Science and Technology, New Delhi, India (SERB-DST, Grant Number EMR/2016/002289) for the financial support and research fellowship (N.S.). We thank Director, CSIR-Indian Institute of Chemical Technology for the support (IICT/Pubs./2020/267).
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Abstract

The reaction of arylvinyl alkoxides with chloro(aryl)carbenes provided the corresponding arylvinyl epoxides that underwent Nazarov cyclization in a catalytic amount of scandium triflate, providing easy access to several highly substituted indenes, including some resveratrol-derived natural products.

Key words

Nazarov cyclization - arylvinyl alcohol - arylvinyl epoxides - indenes - resveratrol-derived natural products - scandium triflate - chloro(aryl)carbenes

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705974.
  • Supporting Information


Publication History

Received: 14 September 2020

Accepted after revision: 15 October 2020

Article published online:
13 November 2020

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