Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines

Daniele Simoni; Marinella Roberti; Riccardo Rondanin; Alan P. Kozikowski

doi:10.1016/S0040-4039(99)00763-7

Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines

Daniele Simoni, Marinella Roberti, Riccardo Rondanin, Alan P. Kozikowski

School of Medicine

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

The enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3- one with chiral lithium amides 5 and 6, in the presence of LiCl, gave the chiral lithium enolates which were in turn reacted with methyl cyanoformate. The resulting chiral β-keto esters were reduced with sodium amalgam to afford the 8-oxa-ecgonine- and 8-oxa-pseudoecgonine-like derivatives which allowed facile preparation of the (+)- and (-)-8-oxa-norcocaines and (+)- and (-)-8-oxa-pseudonorcocaines. The new synthesized 8-oxa analogues of cocaine showed good enantiomeric excesses in the range of 84-90%.

Original language	English (US)
Pages (from-to)	4425-4428
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	23
DOIs	https://doi.org/10.1016/S0040-4039(99)00763-7
State	Published - Jun 4 1999

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines",

abstract = "The enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3- one with chiral lithium amides 5 and 6, in the presence of LiCl, gave the chiral lithium enolates which were in turn reacted with methyl cyanoformate. The resulting chiral β-keto esters were reduced with sodium amalgam to afford the 8-oxa-ecgonine- and 8-oxa-pseudoecgonine-like derivatives which allowed facile preparation of the (+)- and (-)-8-oxa-norcocaines and (+)- and (-)-8-oxa-pseudonorcocaines. The new synthesized 8-oxa analogues of cocaine showed good enantiomeric excesses in the range of 84-90%.",

author = "Daniele Simoni and Marinella Roberti and Riccardo Rondanin and Kozikowski, {Alan P.}",

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T1 - Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one

T2 - Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines

AU - Simoni, Daniele

AU - Roberti, Marinella

AU - Rondanin, Riccardo

AU - Kozikowski, Alan P.

PY - 1999/6/4

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N2 - The enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3- one with chiral lithium amides 5 and 6, in the presence of LiCl, gave the chiral lithium enolates which were in turn reacted with methyl cyanoformate. The resulting chiral β-keto esters were reduced with sodium amalgam to afford the 8-oxa-ecgonine- and 8-oxa-pseudoecgonine-like derivatives which allowed facile preparation of the (+)- and (-)-8-oxa-norcocaines and (+)- and (-)-8-oxa-pseudonorcocaines. The new synthesized 8-oxa analogues of cocaine showed good enantiomeric excesses in the range of 84-90%.

AB - The enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3- one with chiral lithium amides 5 and 6, in the presence of LiCl, gave the chiral lithium enolates which were in turn reacted with methyl cyanoformate. The resulting chiral β-keto esters were reduced with sodium amalgam to afford the 8-oxa-ecgonine- and 8-oxa-pseudoecgonine-like derivatives which allowed facile preparation of the (+)- and (-)-8-oxa-norcocaines and (+)- and (-)-8-oxa-pseudonorcocaines. The new synthesized 8-oxa analogues of cocaine showed good enantiomeric excesses in the range of 84-90%.

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Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one: Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines

Abstract

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