Total Synthesis of (+)-13-Deoxytedanolide

In this communication we describe the first total synthesis of (+)-13-deoxytedanolide, an architecturally complex marine macrolide possessing significant antitumor activity. The cornerstone of the synthesis comprises a highly convergent dithiane coupling used to construct the carbon skeleton, follow...

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Veröffentlicht in:	Journal of the American Chemical Society 2003-01, Vol.125 (2), p.350-351
Hauptverfasser:	Smith, Amos B, Adams, Christopher M, Lodise Barbosa, Stephanie A, Degnan, Andrew P
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Antineoplastic agents Antineoplastic Agents - chemical synthesis Biological and medical sciences Chemistry Exact sciences and technology General aspects Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Macrolides - chemical synthesis Medical sciences Nuclear Magnetic Resonance, Biomolecular Organic chemistry Pharmacology. Drug treatments Porifera - chemistry Preparations and properties
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Beschreibung
Zusammenfassung:	In this communication we describe the first total synthesis of (+)-13-deoxytedanolide, an architecturally complex marine macrolide possessing significant antitumor activity. The cornerstone of the synthesis comprises a highly convergent dithiane coupling used to construct the carbon skeleton, followed by a novel use of the Evans−Tishchenko reduction to oxidize the C(1) aldehyde to an ester in the presence of the oxidatively labile dithiane.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja0289649