1,6-Asymmetric Induction in Boron-Mediated Aldol Reactions:  Application to a Practical Total Synthesis of (+)-Discodermolide

1,6-Asymmetric Induction in Boron-Mediated Aldol Reactions:  Application to a Practical Total Synthesis of (+)-Discodermolide

By relying solely on substrate-based stereocontrol, a practical total synthesis of the microtubule-stabilizing anticancer agent (+)-discodermolide has been realized. This exploits a novel aldol bond construction with 1,6-stereoinduction from the boron enolate of (Z)-enone 3 in addition to aldehyde 2...

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Veröffentlicht in:Organic letters 2003-01, Vol.5 (1), p.35-38
Hauptverfasser: Paterson, Ian, Delgado, Oscar, Florence, Gordon J., Lyothier, Isabelle, Scott, Jeremy P., Sereinig, Natascha
Format: Artikel
Sprache:eng
Schlagworte:
Alkanes
Animals
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Boron - chemistry
Carbamates
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Porifera
Pyrones
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Zusammenfassung:By relying solely on substrate-based stereocontrol, a practical total synthesis of the microtubule-stabilizing anticancer agent (+)-discodermolide has been realized. This exploits a novel aldol bond construction with 1,6-stereoinduction from the boron enolate of (Z)-enone 3 in addition to aldehyde 2. The 1,3-diol 7 is employed as a common building block for the C1−C5, C9−C16, and C17−C24 subunits.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0270780