Stereocontrolled syntheses of (-)-goniofufurone and (-)-8-epi-goniofufurone

Tony Kung Ming Shing, Hon Chung Tsui, Zhao Hui Zhou

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The absolute configurations of natural goniofufurone and 8-epi-goniofufurone are shown to be 2 and 4 respectively by unambiguous syntheses of their enantiomers 1 and 3 from d-glycero-d-gulo-heptono-γ-lactone 7 involving an intramolecular Michael reaction as the key step. The diol 6, readily availble from d-glycero-d-gulo-heptono-γ-lactone, has been converted by six sequential reactions (acetylation, hydrolysis, deacetylation, glycol cleavage, Wittig reaction, and hydrolysis) into the γ-lactone 5 which underwent an intramolecular Michael reaction to yield (-)-goniofufurone 1. Likewise reactions of the monoacetate 12 gave (-)-8-epi-goniofufurone 3.

Original languageEnglish
Pages (from-to)8659-8666
Number of pages8
JournalTetrahedron
Volume48
Issue number40
DOIs
Publication statusPublished - 1992 Jan 1
Externally publishedYes

Fingerprint

Lactones
Mustelidae
Hydrolysis
Acetylation
Glycols
Enantiomers
7-goniofufurone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Stereocontrolled syntheses of (-)-goniofufurone and (-)-8-epi-goniofufurone. / Shing, Tony Kung Ming; Tsui, Hon Chung; Zhou, Zhao Hui.

In: Tetrahedron, Vol. 48, No. 40, 01.01.1992, p. 8659-8666.

Research output: Contribution to journalArticle

Shing, Tony Kung Ming ; Tsui, Hon Chung ; Zhou, Zhao Hui. / Stereocontrolled syntheses of (-)-goniofufurone and (-)-8-epi-goniofufurone. In: Tetrahedron. 1992 ; Vol. 48, No. 40. pp. 8659-8666.
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