Novel radical synthesis of morphine fragments spiro[benzofuran-3(2H),4'-piperidine] and octahydro-1H-benzofuro[3,2-e]isoquinoline

Chen Yu Cheng, Ling Wei Hsin, Jing Ping Liou

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

A new strategy for the synthesis of oxide-containing fragments of morphine has been developed. Thus, the tricyclic (ANO) morphine fragment spiro[7-methoxybenzofuran-3(2H),4'-1'-methylpiperidine] (1) was obtained as the sole product via an intramolecular radical cyclization of 4-[(2'-bromo-6'-methoxyphenoxyl)methyl]-1-methyl-1,2,5,6-tetrahydropyr idine (9); while the tetrayclic (ACNO) fragmet 9-methoxy-3-methyl-2,3,4,4aα,5,6,7,7aα-octahydro-1H-benzofuro[3,2-e] isoquinoline (3) and its 4-oxo analog 4 were synthesized in a similar fashion starting from 5,6,7,8-tetrahydroisoquinoline (10).

Original languageEnglish
Pages (from-to)10935-10944
Number of pages10
JournalTetrahedron
Volume52
Issue number33
DOIs
Publication statusPublished - Aug 12 1996
Externally publishedYes

Fingerprint

Morphine
Tetrahydroisoquinolines
Cyclization
Oxides
isoquinoline
benzofuran
piperidine
N-methylpiperidine
4-methylpiperidine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Novel radical synthesis of morphine fragments spiro[benzofuran-3(2H),4'-piperidine] and octahydro-1H-benzofuro[3,2-e]isoquinoline. / Cheng, Chen Yu; Hsin, Ling Wei; Liou, Jing Ping.

In: Tetrahedron, Vol. 52, No. 33, 12.08.1996, p. 10935-10944.

Research output: Contribution to journalArticle

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abstract = "A new strategy for the synthesis of oxide-containing fragments of morphine has been developed. Thus, the tricyclic (ANO) morphine fragment spiro[7-methoxybenzofuran-3(2H),4'-1'-methylpiperidine] (1) was obtained as the sole product via an intramolecular radical cyclization of 4-[(2'-bromo-6'-methoxyphenoxyl)methyl]-1-methyl-1,2,5,6-tetrahydropyr idine (9); while the tetrayclic (ACNO) fragmet 9-methoxy-3-methyl-2,3,4,4aα,5,6,7,7aα-octahydro-1H-benzofuro[3,2-e] isoquinoline (3) and its 4-oxo analog 4 were synthesized in a similar fashion starting from 5,6,7,8-tetrahydroisoquinoline (10).",
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N2 - A new strategy for the synthesis of oxide-containing fragments of morphine has been developed. Thus, the tricyclic (ANO) morphine fragment spiro[7-methoxybenzofuran-3(2H),4'-1'-methylpiperidine] (1) was obtained as the sole product via an intramolecular radical cyclization of 4-[(2'-bromo-6'-methoxyphenoxyl)methyl]-1-methyl-1,2,5,6-tetrahydropyr idine (9); while the tetrayclic (ACNO) fragmet 9-methoxy-3-methyl-2,3,4,4aα,5,6,7,7aα-octahydro-1H-benzofuro[3,2-e] isoquinoline (3) and its 4-oxo analog 4 were synthesized in a similar fashion starting from 5,6,7,8-tetrahydroisoquinoline (10).

AB - A new strategy for the synthesis of oxide-containing fragments of morphine has been developed. Thus, the tricyclic (ANO) morphine fragment spiro[7-methoxybenzofuran-3(2H),4'-1'-methylpiperidine] (1) was obtained as the sole product via an intramolecular radical cyclization of 4-[(2'-bromo-6'-methoxyphenoxyl)methyl]-1-methyl-1,2,5,6-tetrahydropyr idine (9); while the tetrayclic (ACNO) fragmet 9-methoxy-3-methyl-2,3,4,4aα,5,6,7,7aα-octahydro-1H-benzofuro[3,2-e] isoquinoline (3) and its 4-oxo analog 4 were synthesized in a similar fashion starting from 5,6,7,8-tetrahydroisoquinoline (10).

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