Diacetone-glucose architecture as a chirality template. Part 9. Enantioselectiye synthesis of (R)-mevalonolactone and (R)-[2H9]mevalonolactone on carbohydrate template

Masashi Kishida, Noriaki Yamauchi, Keiju Sawada, Yuji Ohashi, Tadashi Eguchi, Katsumi Kakinuma

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A highly enantioselective synthetic methodology for (R)-mevalonolactone has been developed based upon the chirality-transcription approach using a chiral template, diacetone-D-glucos-3-ulose 2. (R)-Mevalonolactone 1a is prepared from ketone 2 in 5 steps in 11% overall yield. This methodology is further applied to the synthesis of fully deuteriated (R)-[2H9]mevalonolactone 1b starting from ketone 2 and methyl [2H7]senecioate 7.

Original languageEnglish
Pages (from-to)891-895
Number of pages5
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number6
DOIs
Publication statusPublished - Mar 21 1997
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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