The enantiodivergent synthesis of Streptomyces alkaloid 4-epi-SS20846A was based on a Takai olefination/Suzuki-Miyaura coupling sequence for the highly stereoselective introduction of the E,E pentadienyl side chain on the piperidine skeleton. Optical separation of a key hydroxylated enamide ester, prepared by Pd-catalyzed methoxycarbonylation of a lactam-derived enol phosphate, was successfully achieved by both lipase-catalyzed kinetic resolution and semi-preparative HPLC. This approach allowed us to obtain the enantiopure target alkaloid in 35-38% yield over six steps.

Synthesis of Both Enantiomers of the Streptomyces Alkaloid 4-epi-SS20846A / Dina Scarpi; Ottavia Avataneo; Cristina Prandi; Paolo Venturello; Ernesto Occhiato. - In: SYNTHESIS. - ISSN 0039-7881. - STAMPA. - 44:(2012), pp. 3688-3692. [10.1055/s-0032-1317490]

Synthesis of Both Enantiomers of the Streptomyces Alkaloid 4-epi-SS20846A

SCARPI, DINA;OCCHIATO, ERNESTO GIOVANNI
2012

Abstract

The enantiodivergent synthesis of Streptomyces alkaloid 4-epi-SS20846A was based on a Takai olefination/Suzuki-Miyaura coupling sequence for the highly stereoselective introduction of the E,E pentadienyl side chain on the piperidine skeleton. Optical separation of a key hydroxylated enamide ester, prepared by Pd-catalyzed methoxycarbonylation of a lactam-derived enol phosphate, was successfully achieved by both lipase-catalyzed kinetic resolution and semi-preparative HPLC. This approach allowed us to obtain the enantiopure target alkaloid in 35-38% yield over six steps.
2012
44
3688
3692
Dina Scarpi; Ottavia Avataneo; Cristina Prandi; Paolo Venturello; Ernesto Occhiato
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/782359
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