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Synthesis 2010(14): 2419-2423  
DOI: 10.1055/s-0029-1218784
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (±)-Diospongin A: A Hetero-Diels-Alder and C-Glycosylation Approach

Jesse D. More*
Department of Chemistry, Loyola University Maryland, 4501 North Charles Street, Baltimore, MD 21210, USA
Fax: +1(410)6172803; e-Mail: jdmore@loyola.edu;
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Publikationsverlauf

Received 21 January 2010
Publikationsdatum:
10. Mai 2010 (online)

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Abstract

The racemic natural product diospongin A has been prepared using a short and stereoselective sequence. Key steps include a hetero-Diels-Alder reaction and an anchimeric assistance-controlled C-glycosylation

Key words

Diels-Alder reaction - glycosylation - neighboring-group effects - natural products

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Sawant and Jennings also synthesized 1 by reduction of an analogous oxocarbenium ion. See ref. 2i.