Synthesis 2019; 51(21): 3989-3997
DOI: 10.1055/s-0039-1690179
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Aza-polyquinanes via Fischer Indolization and Ring-Rearrangement Metathesis as Key Steps

Sambasivarao Kotha
Department of Chemistry, Indian Institute of Technology-Bombay, Powai, India   Email: srk@chem.iitb.ac.in
,
Ramakrishna Reddy Keesari
,
Saima Ansari
› Author Affiliations
We thank the Defence Research and Development Organisation (DRDO; Project Code. RD/0117-ARDB000-004), New Delhi, India for financial assistance. S.K. thanks the Department of Science and Technology for the award of a J.C. Bose fellowship (SR/S2/JCB-33/2010), Praj industries, Pune, for Pramod Chaudhari Chair Professorship (Green Chemistry). R.R.K. thanks the Defence Research and Development Organisation (DRDO), New Delhi, India. S.A. thanks the University Grants Commission (UGC) for a fellowship.
Further Information

Publication History

Received: 03 May 2019

Accepted after revision: 25 July 2019

Publication Date:
26 August 2019 (online)

Abstract

Herein, we describe a simple synthetic strategy to assemble aza-polyquinane systems containing an indole motif by employing the Fischer indolization and ring-rearrangement metathesis as key steps. The precursor used here is exo-dicyclopentadienone, which is derived from less explored exo-dicyclopentadiene. By using this approach, several aza-polyquinanes that contain indole units and fused medium rings (eight- and nine-membered rings) were synthesized in good yields.

Supporting Information

 
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