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Synthesis 2010(20): 3449-3452  
DOI: 10.1055/s-0030-1258201
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Total Synthesis of (+)-Varitriol from d-Ribonolactone

Ol’ga Karlubíková, Miroslav Palík, Angelika Lásiková, Tibor Gracza*
Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovak Republic
e-Mail: tibor.gracza@stuba.sk;
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Publikationsverlauf

Received 11 May 2010
Publikationsdatum:
09. August 2010 (online)

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Abstract

A short and efficient total synthesis of cytotoxic natural (+)-varitriol has been accomplished in eight steps from γ-d-ribonolactone and 2,3-dimethylanisole in 41% overall yield. The key features include a highly stereoselective introduction of methyl at a carbonyl group and installation of the side chain with the aromatic portion by Julia-Kocieński olefination at C5 of the starting carbon skeleton.

Key words

natural products - varitriol - stereoselective synthesis - diastereoselectivity - chiral pool

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