Total Synthesis of the Potent Microtubule-Stabilizing Agent (+)-Discodermolide

The total synthesis of the potent microtubule-stabilizing, antimitotic agent (+)-discodermolide is described. The convergent synthetic strategy takes advantage of the diastereoselective alkylation of a ketone enolate to establish the key C15−C16 bond. The synthesis is amenable to preparation of gram...

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Veröffentlicht in:	Journal of organic chemistry 2003-08, Vol.68 (17), p.6646-6660
Hauptverfasser:	Harried, Scott S, Lee, Christopher P, Yang, Ge, Lee, Tony I. H, Myles, David C
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkanes - chemical synthesis Alkanes - chemistry Alkanes - pharmacology Alkylation Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Carbamates - chemical synthesis Carbamates - chemistry Carbamates - pharmacology Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Indicators and Reagents Lactones - chemical synthesis Lactones - chemistry Lactones - pharmacology Microtubules - drug effects Microtubules - ultrastructure Models, Molecular Molecular Conformation Organic chemistry Preparations and properties Pyrones
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Zusammenfassung:	The total synthesis of the potent microtubule-stabilizing, antimitotic agent (+)-discodermolide is described. The convergent synthetic strategy takes advantage of the diastereoselective alkylation of a ketone enolate to establish the key C15−C16 bond. The synthesis is amenable to preparation of gram-scale quantities of (+)-discodermolide and analogues.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo034521r