Synthesis of morphine fragments spiro[benzofuran-3(2H),4'-piperidine] and octahydro-1H-benzofuro[3,2-e]isoquinoline by intramolecular heck reaction

Chen Yu Cheng, Jing Ping Liou, Mei Jing Lee

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

As a better alternative to radical cyclization, 5-(2-bromo-6-methoxyphenoxy)-2-methyl-1 ,2,3,4,5,6,7,8-octahydroisoquinoline (2) and its 1-oxo analog 3 underwent Pd-catalyzed intramolecular cyclization to give the tetracyclic (ACNO) morphine fragments 5 and 6 respectively. 4-[(2'-Iodo-6'-methoxyphenoxy)methyl]-1-ethoxycarbonyl-1,2,5,6, -tetrahydropyridine (11) reacted similarly to provide the tricyclic ANO fragment 12 in 70% yield and 45% e.e. when a Pd-(S)-BINAP complex was used as the catalyst.

Original languageEnglish
Pages (from-to)4571-4574
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number26
DOIs
Publication statusPublished - Jun 30 1997
Externally publishedYes

Fingerprint

Cyclization
Morphine
Catalysts
benzofuran
piperidine
isoquinoline
2-naphthol BINAP

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of morphine fragments spiro[benzofuran-3(2H),4'-piperidine] and octahydro-1H-benzofuro[3,2-e]isoquinoline by intramolecular heck reaction. / Cheng, Chen Yu; Liou, Jing Ping; Lee, Mei Jing.

In: Tetrahedron Letters, Vol. 38, No. 26, 30.06.1997, p. 4571-4574.

Research output: Contribution to journalArticle

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