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

Tony K.M. Shing, Hon Chung Tsui, Zhao Hui Zhou

Research output: Contribution to journalArticle

27 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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Stereocontrolled syntheses of (-)-goniofufurone and (-)-8-epi-goniofufurone'. Together they form a unique fingerprint.

  • Cite this