Carbocyclization of carbohydrates

Diastereoselective synthesis of (+)-gabosine F, (-)-gabosine O, and (+)-4-epi-gabosine O

Tony Kung Ming Shing, King H. So, Wun S. Kwok

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Exploitation of silica gel/chloramine T mediated intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar-derived oxlmes to carbocycles furnished the first synthesis of gaboslne F from L-arablnose In 12 steps with 23% overall yield, thereby confirming Its absolute configuration. Similarly, efficient syntheses of gaboslne O and 4-epl-gaboslne O were accomplished from D-mannose In 9 and 11 steps with 41% and 38% overall yields, respectively, involving INOC, regeoselective dehydration, and dlastereoselective hydrogenation as the key steps.

Original languageEnglish
Pages (from-to)5070-5073
Number of pages4
JournalOrganic Letters
Volume11
Issue number21
DOIs
Publication statusPublished - 2009 Nov 5
Externally publishedYes

Fingerprint

Nitriles
Cycloaddition
carbohydrates
Cycloaddition Reaction
Alkenes
Oxides
nitriles
Carbohydrates
cycloaddition
alkenes
Hydrogenation
Silica Gel
synthesis
Mannose
Dehydration
Sugars
oxides
silica gel
sugars
exploitation

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Carbocyclization of carbohydrates : Diastereoselective synthesis of (+)-gabosine F, (-)-gabosine O, and (+)-4-epi-gabosine O. / Shing, Tony Kung Ming; So, King H.; Kwok, Wun S.

In: Organic Letters, Vol. 11, No. 21, 05.11.2009, p. 5070-5073.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; So, King H. ; Kwok, Wun S. / Carbocyclization of carbohydrates : Diastereoselective synthesis of (+)-gabosine F, (-)-gabosine O, and (+)-4-epi-gabosine O. In: Organic Letters. 2009 ; Vol. 11, No. 21. pp. 5070-5073.
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