(-)-Quinic acid in organic synthesis. Part 4. Syntheses of cyclophellitol and its (1R, 6S)-, (2S)-, (1R, 2S, 6S)-diastereoisomers

Tony K.M. Shing, Vincent W.F. Tai

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Cyclophellitol 1 and its (1R, 6S)-, (2S)-, (1R, 2S, 6S)-diastereoisomers 2, 3 and 4 are constructed from quinic acid involving the following key steps: regioselective cyclic sulfate ring opening, regiospecific oxidative elimination and an epoxidation. Diastereoisomers 1, 2, 3 and 4 are characterized as their corresponding tetraacetates 5, 6, 7 and 8.

Original languageEnglish
Pages (from-to)2017-2025
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
Publication statusPublished - 1994 Jan 1

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of '(-)-Quinic acid in organic synthesis. Part 4. Syntheses of cyclophellitol and its (1R, 6S)-, (2S)-, (1R, 2S, 6S)-diastereoisomers'. Together they form a unique fingerprint.

  • Cite this