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
Publication statusPublished - Mar 21 1997
Externally publishedYes

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Chirality
Carbohydrates
Ketones
Transcription
mevalonolactone
1,2-5,6-di-O-isopropylidene-D-glucofuranose

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Diacetone-glucose architecture as a chirality template. Part 9. Enantioselectiye synthesis of (R)-mevalonolactone and (R)-[2H9]mevalonolactone on carbohydrate template. / Kishida, Masashi; Yamauchi, Noriaki; Sawada, Keiju; Ohashi, Yuji; Eguchi, Tadashi; Kakinuma, Katsumi.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 6, 21.03.1997, p. 891-895.

Research output: Contribution to journalArticle

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AU - Eguchi, Tadashi

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