Regioselective Mukaiyama hydroperoxysilylation of 2-alkyl- or 2-aryl-prop-2-en-1-ols: application to a new synthesis of 1,2,4-trioxanes

O'Neill, P. M., Pugh, M., Davies, Jill, Ward, Stephen ORCID: https://orcid.org/0000-0003-2331-3192 and Park, B. K. (2001) 'Regioselective Mukaiyama hydroperoxysilylation of 2-alkyl- or 2-aryl-prop-2-en-1-ols: application to a new synthesis of 1,2,4-trioxanes'. Tetrahedron Letters, Vol 42, Issue 27, pp. 4569-4571.

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Abstract

Co(II)-mediated peroxysilylation of allylic alcohols 6 or 9 regioselectively provides peroxysilyl alcohols 7 and 10 in good yield. Reaction of these peroxysilyl alcohols with aldehydes or ketones provides target 1,2,4-trioxanes in good to excellent yields. The sequence of Markovnikov hydroperoxysilylation and subsequent reaction with a carbonyl compound can also be readily achieved in a one-pot procedure. Significantly, easily prepared trioxanes 11a and 11b have potent in vitro antimalarial activity versus chloroquine resistant K1 Plasmodium falciparum.

Item Type:	Article
Subjects:	QV Pharmacology > Anti-Inflammatory Agents. Anti-Infective Agents. Antineoplastic Agents > QV 256 Antimalarials WA Public Health > Preventive Medicine > WA 110 Prevention and control of communicable diseases. Transmission of infectious diseases WC Communicable Diseases > Tropical and Parasitic Diseases > WC 750 Malaria
Faculty: Department:	Pre 2002
Digital Object Identifer (DOI):	https://doi.org/10.1016/s0040-4039(01)00791-2
Depositing User:	Lynn Roberts-Maloney
Date Deposited:	17 Oct 2013 10:59
Last Modified:	06 Feb 2018 13:05
URI:	https://archive.lstmed.ac.uk/id/eprint/3182

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