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 | |
| State | Published - Jun 4 1999 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Enantioselective deprotonation of the 8-oxabicyclo[3.2.1]octan-3-one : Synthesis of 8-oxa-norcocaines and 8-oxa-pseudonorcocaines. / Simoni, Daniele; Roberti, Marinella; Rondanin, Riccardo; Kozikowski, Alan P.
In: Tetrahedron Letters, Vol. 40, No. 23, 04.06.1999, p. 4425-4428.Research output: Contribution to journal › Article
}
TY - JOUR
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
Y1 - 1999/6/4
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%.
UR - http://www.scopus.com/inward/record.url?scp=0033523049&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033523049&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(99)00763-7
DO - 10.1016/S0040-4039(99)00763-7
M3 - Article
AN - SCOPUS:0033523049
VL - 40
SP - 4425
EP - 4428
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 23
ER -