Approach to the hyacinthacines: first non-chiral pool synthesis of (+)-hyacinthacine A1

Approach to the hyacinthacines: first non-chiral pool synthesis of (+)-hyacinthacine A1

The first non-chiral pool total synthesis of (+)-hyacinthacine A(1) is described. This synthesis is based on an effective [2 + 2] cycloaddition of dichloroketene to a Stericol-based enol ether, a diastereoselective dihydroxylation, and an efficient Tamao-Fleming oxidation.

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Veröffentlicht in:Organic & biomolecular chemistry 2008, Vol.6 (7), p.1170-1172
Hauptverfasser: Reddy, P Venkatram, Veyron, Amaël, Koos, Peter, Bayle, Alexandre, Greene, Andrew E, Delair, Philippe
Format: Artikel
Sprache:eng
Schlagworte:
Cyclization
Dichloroethylenes - chemistry
Molecular Structure
Pyrrolizidine Alkaloids - chemical synthesis
Pyrrolizidine Alkaloids - chemistry
Stereoisomerism
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Zusammenfassung:The first non-chiral pool total synthesis of (+)-hyacinthacine A(1) is described. This synthesis is based on an effective [2 + 2] cycloaddition of dichloroketene to a Stericol-based enol ether, a diastereoselective dihydroxylation, and an efficient Tamao-Fleming oxidation.
ISSN:1477-0520
1477-0539
DOI:10.1039/b800445e