Issue 17, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

π-Allyl cation cyclisations initiated by electrocyclic ring-opening of gem-dihalocyclopropanes: application to the first total syntheses of the crinine-type alkaloids maritinamine and epi-maritinamine

Martin G. Banwell,*a   Joanne E. Harveya  and  Katrina A. Jolliffea  

* Corresponding authors

a Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, Australia

Abstract

The racemic modifications of the crinine alkaloids 1 and 2 have been synthesized for the first time and by a pathway that involves silver(I)-promoted electrocyclic ring-opening of the ring-fused gem-dichlorocyclopropane 3 and trapping of the resulting π-allyl cation by the tethered carbamate moiety so as to form the pivotal C3a-arylated hexahydroindole 14.

Graphical abstract: π-Allyl cation cyclisations initiated by electrocyclic ring-opening of gem-dihalocyclopropanes: application to the first total syntheses of the crinine-type alkaloids maritinamine and epi-maritinamine

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Article information

DOI
https://doi.org/10.1039/B106369N
Article type
Communication
Submitted
17 Jul 2001
Accepted
30 Jul 2001
First published
13 Aug 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2002-2005

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π-Allyl cation cyclisations initiated by electrocyclic ring-opening of gem-dihalocyclopropanes: application to the first total syntheses of the crinine-type alkaloids maritinamine and epi-maritinamine

M. G. Banwell, J. E. Harvey and K. A. Jolliffe, J. Chem. Soc., Perkin Trans. 1, 2001, 2002 DOI: 10.1039/B106369N

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