Electrooxidative synthesis of morphinandienones from 1-benzyltetrahydroisoquinolines

J R Falck; L. L. Miller; F. R. Stermitz

doi:10.1016/S0040-4020(01)97477-0

Electrooxidative synthesis of morphinandienones from 1-benzyltetrahydroisoquinolines

J R Falck, L. L. Miller, F. R. Stermitz

Biochemistry

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

34 Scopus citations

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	https://doi.org/10.1016/S0040-4020(01)97477-0
State	Published - 1974

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Electrooxidative synthesis of morphinandienones from 1-benzyltetrahydroisoquinolines",

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%).",

author = "Falck, {J R} and Miller, {L. L.} and Stermitz, {F. R.}",

year = "1974",

doi = "10.1016/S0040-4020(01)97477-0",

language = "English (US)",

volume = "30",

pages = "931--934",

journal = "Tetrahedron",

issn = "0040-4020",

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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%).

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DO - 10.1016/S0040-4020(01)97477-0

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EP - 934

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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