Total synthesis of marine natural products separacenes A and B

Total synthesis of marine natural products separacenes A and B

A short and convergent route for the stereoselective total synthesis of separacenes A and B has been developed using (+)-methyl d-lactate and d-(-)-tartaric acid as the chiral pools. The characteristic features of this synthesis include the Trost-Rychnovsky alkyne rearrangement to construct the C -C...

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Veröffentlicht in:Organic & biomolecular chemistry 2017, Vol.15 (22), p.4842-4850
Hauptverfasser: Das, Subhendu, Goswami, Rajib Kumar
Format: Artikel
Sprache:eng
Schlagworte:
Biological Products - chemical synthesis
Biological Products - chemistry
Molecular Structure
Polyenes - chemical synthesis
Polyenes - chemistry
Stereoisomerism
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Zusammenfassung:A short and convergent route for the stereoselective total synthesis of separacenes A and B has been developed using (+)-methyl d-lactate and d-(-)-tartaric acid as the chiral pools. The characteristic features of this synthesis include the Trost-Rychnovsky alkyne rearrangement to construct the C -C conjugated diene, the Horner-Wadsworth-Emmons olefination to form the C -C and C -C olefins and the Corey-Bakshi-Shibata reaction to install the C-13 hydroxy functionality.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob00345e