Conversion of D-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction: Application to Total Synthesis of (+)-Cyclophellitol

Teruhiko Ishikawa; Yoshihiro Shimizu; Takayuki Kudoh; Seiki Saito

doi:10.1021/ol035424n

Conversion of D-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction: Application to Total Synthesis of (+)-Cyclophellitol

Teruhiko Ishikawa, Yoshihiro Shimizu, Takayuki Kudoh, Seiki Saito

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45 Citations (Scopus)

Abstract

(Matrix presented). A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4, 5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cycloaddition on treatment with TMS-CI and Et₃N in the presence of catalytic DMAP followed by acid treatment. (+)-Cyclophellitol (1) was synthesized from B in eight steps.

Original language	English
Pages (from-to)	3879-3882
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	21
DOIs	https://doi.org/10.1021/ol035424n
Publication status	Published - Oct 16 2003

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Conversion of D-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction: Application to Total Synthesis of (+)-Cyclophellitol. / Ishikawa, Teruhiko; Shimizu, Yoshihiro; Kudoh, Takayuki et al.
In: Organic Letters, Vol. 5, No. 21, 16.10.2003, p. 3879-3882.

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

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abstract = "(Matrix presented). A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4, 5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cycloaddition on treatment with TMS-CI and Et3N in the presence of catalytic DMAP followed by acid treatment. (+)-Cyclophellitol (1) was synthesized from B in eight steps.",

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AU - Kudoh, Takayuki

AU - Saito, Seiki

PY - 2003/10/16

Y1 - 2003/10/16

N2 - (Matrix presented). A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4, 5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cycloaddition on treatment with TMS-CI and Et3N in the presence of catalytic DMAP followed by acid treatment. (+)-Cyclophellitol (1) was synthesized from B in eight steps.

AB - (Matrix presented). A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4, 5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cycloaddition on treatment with TMS-CI and Et3N in the presence of catalytic DMAP followed by acid treatment. (+)-Cyclophellitol (1) was synthesized from B in eight steps.

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Conversion of D-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction: Application to Total Synthesis of (+)-Cyclophellitol

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