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Synlett 2013; 24(15): 1921-1926
DOI: 10.1055/s-0033-1339489
letter
© Georg Thieme Verlag Stuttgart · New York

Diversity-Oriented Approach to Novel Spirocyclics via Enyne Metathesis, Diels–Alder Reaction, and a [2+2+2] Cycloaddition as Key Steps

Sambasivarao Kotha*
Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai-400076, India   Fax: +91(22)25727152   Email: srk@chem.iitb.ac.in
,
Rashid Ali
Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai-400076, India   Fax: +91(22)25727152   Email: srk@chem.iitb.ac.in
,
Arti Tiwari
Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai-400076, India   Fax: +91(22)25727152   Email: srk@chem.iitb.ac.in
› Author Affiliations
Further Information

Publication History

Received: 20 March 2013

Accepted after revision: 09 July 2013

Publication Date:
14 August 2013 (online)

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This paper is dedicated to the memory of Professor A. Srikrishna, Department of Organic Chemistry, Indian Institute of Science, Bangalore, India.

Abstract

A simple protocol for the synthesis of indane-based spirocyclics has been developed via enyne metathesis, Diels–Alder reaction, and a [2+2+2] cycloaddition as key steps starting from indane-1,3-dione. The key diene building block was assembled by enyne metathesis. In this sequence, rongalite is used as a green reagent to prepare the sultine intermediate, which is a useful precursor to generate the transient diene.

Keywords

spirocyclic compounds - [2+2+2]-cycloaddition reaction - rongalite - enyne metathesis - Diels–Alder reaction

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

  • References and Notes

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