Chemoenzymatic Approaches to Lycorine-Type Amaryllidaceae Alkaloids:  Total Syntheses of ent-Lycoricidine, 3-epi-ent-Lycoricidine, and 4-Deoxy-3-epi-ent-lycoricidine

Chemoenzymatic Approaches to Lycorine-Type Amaryllidaceae Alkaloids:  Total Syntheses of ent-Lycoricidine, 3-epi-ent-Lycoricidine, and 4-Deoxy-3-epi-ent-lycoricidine

The readily available and enzymatically derived cis-1,2-dihydrocatechol 4 has been elaborated, over 11 steps including an Overman rearrangement, into the non-natural enantiomer, (−)-1, of the alkaloid lycoricidine [(+)-1]. Related chemistries have provided analogues 18, 19, and 26.

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Veröffentlicht in:Organic letters 2007-08, Vol.9 (18), p.3683-3685
Hauptverfasser: Matveenko, Maria, Kokas, Okanya J, Banwell, Martin G, Willis, Anthony C
Format: Artikel
Sprache:eng
Schlagworte:
Amaryllidaceae Alkaloids - chemical synthesis
Amaryllidaceae Alkaloids - chemistry
Catalysis
Enzymes - chemistry
Molecular Structure
Phenanthridines - chemical synthesis
Phenanthridines - chemistry
Stereoisomerism
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Zusammenfassung:The readily available and enzymatically derived cis-1,2-dihydrocatechol 4 has been elaborated, over 11 steps including an Overman rearrangement, into the non-natural enantiomer, (−)-1, of the alkaloid lycoricidine [(+)-1]. Related chemistries have provided analogues 18, 19, and 26.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol701552r