Abstract
The electrochemical oxidation of several 1-benzyl tetrahydroisoquinolines has been performed at a platinum anode in acetonitrile. Using potentiostatic conditions and a three compartment cell, the following cyclizations were accomplished on a several hundred milligram scale in the yields indicated: 6′-bromolaudanosine to O-methylflavinantine (16%), 5′-methoxylaudanosine to O-methyl-C-norandrocymbine (38%), 8-methoxylaudanosine to protostephanone (35%), norlaudanosine to N-nor-O-methylflavinantine (22%).
| Original language | English (US) |
|---|---|
| Pages (from-to) | 931-934 |
| Number of pages | 4 |
| Journal | Tetrahedron |
| Volume | 30 |
| Issue number | 8 |
| DOIs | |
| State | Published - 1974 |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Electrooxidative synthesis of morphinandienones from 1-benzyltetrahydroisoquinolines. / Falck, J R; Miller, L. L.; Stermitz, F. R.
In: Tetrahedron, Vol. 30, No. 8, 1974, p. 931-934.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Electrooxidative synthesis of morphinandienones from 1-benzyltetrahydroisoquinolines
AU - Falck, J R
AU - Miller, L. L.
AU - Stermitz, F. R.
PY - 1974
Y1 - 1974
N2 - The electrochemical oxidation of several 1-benzyl tetrahydroisoquinolines has been performed at a platinum anode in acetonitrile. Using potentiostatic conditions and a three compartment cell, the following cyclizations were accomplished on a several hundred milligram scale in the yields indicated: 6′-bromolaudanosine to O-methylflavinantine (16%), 5′-methoxylaudanosine to O-methyl-C-norandrocymbine (38%), 8-methoxylaudanosine to protostephanone (35%), norlaudanosine to N-nor-O-methylflavinantine (22%).
AB - The electrochemical oxidation of several 1-benzyl tetrahydroisoquinolines has been performed at a platinum anode in acetonitrile. Using potentiostatic conditions and a three compartment cell, the following cyclizations were accomplished on a several hundred milligram scale in the yields indicated: 6′-bromolaudanosine to O-methylflavinantine (16%), 5′-methoxylaudanosine to O-methyl-C-norandrocymbine (38%), 8-methoxylaudanosine to protostephanone (35%), norlaudanosine to N-nor-O-methylflavinantine (22%).
UR - http://www.scopus.com/inward/record.url?scp=0000733082&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0000733082&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)97477-0
DO - 10.1016/S0040-4020(01)97477-0
M3 - Article
AN - SCOPUS:0000733082
VL - 30
SP - 931
EP - 934
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 8
ER -