A Second-Generation Total Synthesis of Spirastrellolide A Methyl Ester

A Second-Generation Total Synthesis of Spirastrellolide A Methyl Ester

Marine macrolides: An improved second‐generation total synthesis of the anticancer macrolide spirastrellolide A methyl ester has been achieved. The synthesis features a uniformly high level of stereocontrol combined with more expedient fragment assembly, and demonstrates a critical dependence of the...

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Veröffentlicht in:Angewandte Chemie International Edition 2012-03, Vol.51 (11), p.2749-2753
Hauptverfasser: Paterson, Ian, Maltas, Philip, Dalby, Stephen M., Lim, Jong Ho, Anderson, Edward A.
Format: Artikel
Sprache:eng
Schlagworte:
Acetals - chemistry
anticancer agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Assembly
Esters
Fragmentation
Level (quantity)
Macrolides - chemical synthesis
Macrolides - chemistry
Marine
marine macrolides
natural products
Spiro Compounds
spiroacetals
Synthesis
total synthesis
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Beschreibung
Zusammenfassung:Marine macrolides: An improved second‐generation total synthesis of the anticancer macrolide spirastrellolide A methyl ester has been achieved. The synthesis features a uniformly high level of stereocontrol combined with more expedient fragment assembly, and demonstrates a critical dependence of the crucial macrolactonization step on the substitution pattern of the C22–C24 linker region.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201108594