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Synthesis 2010(14): 2419-2423
DOI: 10.1055/s-0029-1218784
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
Further Information
Received
21 January 2010
Publication Date:
10 May 2010 (online)
Publication History
Publication Date:
10 May 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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References
Sawant and Jennings also synthesized 1 by reduction of an analogous oxocarbenium ion. See ref. 2i.