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

doi:10.1039/a606208c

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 journal › Article › peer-review

21 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 language	English
Pages (from-to)	891-895
Number of pages	5
Journal	Journal of the Chemical Society - Perkin Transactions 1
Issue number	6
DOIs	https://doi.org/10.1039/a606208c
Publication status	Published - Mar 21 1997
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1039/a606208c

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

Research output: Contribution to journal › Article › peer-review

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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.",

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AU - Sawada, Keiju

AU - Ohashi, Yuji

AU - Eguchi, Tadashi

AU - Kakinuma, Katsumi

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AB - 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.

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

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