Expeditious synthesis of new 3,4,6-trihydroxythiepanes from D-(-)-quinic acid

Tzenge Lien Shih*, Yi Chuan Fang

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

10 Scopus citations


We report herein that the new seven-membered-ring thiosugars (thiepanes) have been synthesized from D-(-)-quinic acid. The key feature of the synthesis involves the thiocyclization of protected hexane-1,2,3,5,6-pentanol derivatives. The subsequent step of acidic removal of protecting groups is critical in the reaction conditions to obtain the required 3,4,6-trihydroxythiepanes. During the course of studies, the unexpected trihydroxythiopyrans are formed because of the ring contractions of their corresponding trihydroxythiepanes under various conditions.

Original languageEnglish
Pages (from-to)3337-3349
Number of pages13
JournalSynthetic Communications
Issue number19
StatePublished - 01 2007
Externally publishedYes


  • Quinic acid
  • Thiepane
  • Thiosugar


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