Facile and enantiospecific syntheses of (6 S,7 R)-6-chloro-7-BENZYLOXY-, (7 S)-halo-, and (7 S)-hydroxy-cocaine and natural (-)-cocaine from d -(-)-ribose

Tony Kung Ming Shing, King H. So

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

First syntheses of C6,7 and C7 enantiopure cocaine analogues were achieved from d-(-)-ribose via a trans-acetonide controlled endo-selective intramolecular nitrone-alkene cycloaddition (INAC) as the key step. This synthetic scheme allows practical preparation of cocaine analogues for bioevaluation as potential candidates for the treatment of cocaine addiction and as potential conjugates for immunotherapy.

Original languageEnglish
Pages (from-to)2916-2919
Number of pages4
JournalOrganic Letters
Volume13
Issue number11
DOIs
Publication statusPublished - 2011 Jun 3
Externally publishedYes

Fingerprint

ribose
Ribose
Cocaine
halos
analogs
Cocaine-Related Disorders
Cycloaddition Reaction
cycloaddition
Alkenes
synthesis
Immunotherapy
alkenes
Cycloaddition
preparation
Therapeutics
nitrones

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Facile and enantiospecific syntheses of (6 S,7 R)-6-chloro-7-BENZYLOXY-, (7 S)-halo-, and (7 S)-hydroxy-cocaine and natural (-)-cocaine from d -(-)-ribose. / Shing, Tony Kung Ming; So, King H.

In: Organic Letters, Vol. 13, No. 11, 03.06.2011, p. 2916-2919.

Research output: Contribution to journalArticle

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