Total synthesis of (±)-desoxycodeine-D

A novel route to the morphine skeleton

Jing Ping Liou, Chen Y. Cheng

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

A novel approach towards the construction of the morphine skeleton was demonstrated by a total synthesis of (±)-desoxycodeine-D (11) from 5,6,7,8- tetrahydroisoquinoline and isovanillin. The key steps are two consecutive Pd- catalyzed cyclizations and a Stevens rearrangement for the formation of ring B. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)915-918
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number6
DOIs
Publication statusPublished - Feb 5 2000
Externally publishedYes

Fingerprint

Tetrahydroisoquinolines
Cyclization
Skeleton
Morphine
isovanillin

Keywords

  • Alkaloids
  • Analgesics
  • Palladium
  • Palladium compounds
  • Rearrangements

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Total synthesis of (±)-desoxycodeine-D : A novel route to the morphine skeleton. / Liou, Jing Ping; Cheng, Chen Y.

In: Tetrahedron Letters, Vol. 41, No. 6, 05.02.2000, p. 915-918.

Research output: Contribution to journalArticle

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