Universität zu Köln

Griesbeck, Axel G. and Schlundt, Viktor (2011). 5-Adamantylated 1,2,4-Trioxanes: Adamantane Position is Crucial for Antiparasitic Activity. Synlett (16). S. 2430 - 2433. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-2096

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Abstract

Allylic alcohols with 1'- and 2'-adamantanyl functionalization, available by reaction of 3-methylcrotonaldehyde with 1- and 2-bromoadamantane, respectively, were reacted with singlet oxygen under solution conditions with high diastereoselectivities to give the beta-hydroperoxy alcohols. Lewis acid catalyzed peroxyacetalization of the beta-hydroperoxy alcohols resulted in two sets of 1,2,4-trioxanes. The allylic alcohol 11 delivered the rearrangement product - the less strained primary hydroperoxide - upon singlet oxygenation and Lewis acid treatment.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Griesbeck, Axel G. UNSPECIFIED UNSPECIFIED UNSPECIFIED Schlundt, Viktor UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-488187
DOI:	10.1055/s-0030-1261225
Journal or Publication Title:	Synlett
Number:	16
Page Range:	S. 2430 - 2433
Date:	2011
Publisher:	GEORG THIEME VERLAG KG
Place of Publication:	STUTTGART
ISSN:	1437-2096
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language MEDICINAL CHEMISTRY; BIOLOGICAL-ACTIVITY; ALLYLIC ALCOHOLS; ARTEMISININ; PHOTOOXYGENATION; MALARIA; DERIVATIVES; PEROXIDES; QINGHAOSU; DRUG Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/48818