Synthesis and absolute configuration of the naturally occurring cyano glucoside simmondsin

Noritaka Chida, Ken Yamada, Seiichiro Ogawa

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The synthesis of the naturally occurring cyano glucoside simmondsin, 1, is reported. An optically active cyclitol, L-quebrachitol 2, was stereoselectively converted into the aglycone 19, which was condensed with D-glucose, followed by deprotection to provide simmondsin 1. This synthesis successfully determined the absolute configuration of the natural product.

Original languageEnglish
Pages (from-to)1131-1137
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number9
Publication statusPublished - 1992

Fingerprint

Glucosides
Cyclitols
Biological Products
Glucose
simmondsin
quebrachitol

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis and absolute configuration of the naturally occurring cyano glucoside simmondsin. / Chida, Noritaka; Yamada, Ken; Ogawa, Seiichiro.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 9, 1992, p. 1131-1137.

Research output: Contribution to journalArticle

@article{895dacd7a4614bf3a573148f37866d68,
title = "Synthesis and absolute configuration of the naturally occurring cyano glucoside simmondsin",
abstract = "The synthesis of the naturally occurring cyano glucoside simmondsin, 1, is reported. An optically active cyclitol, L-quebrachitol 2, was stereoselectively converted into the aglycone 19, which was condensed with D-glucose, followed by deprotection to provide simmondsin 1. This synthesis successfully determined the absolute configuration of the natural product.",
author = "Noritaka Chida and Ken Yamada and Seiichiro Ogawa",
year = "1992",
language = "English",
pages = "1131--1137",
journal = "Journal of the Chemical Society. Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",
number = "9",

}

TY - JOUR

T1 - Synthesis and absolute configuration of the naturally occurring cyano glucoside simmondsin

AU - Chida, Noritaka

AU - Yamada, Ken

AU - Ogawa, Seiichiro

PY - 1992

Y1 - 1992

N2 - The synthesis of the naturally occurring cyano glucoside simmondsin, 1, is reported. An optically active cyclitol, L-quebrachitol 2, was stereoselectively converted into the aglycone 19, which was condensed with D-glucose, followed by deprotection to provide simmondsin 1. This synthesis successfully determined the absolute configuration of the natural product.

AB - The synthesis of the naturally occurring cyano glucoside simmondsin, 1, is reported. An optically active cyclitol, L-quebrachitol 2, was stereoselectively converted into the aglycone 19, which was condensed with D-glucose, followed by deprotection to provide simmondsin 1. This synthesis successfully determined the absolute configuration of the natural product.

UR - http://www.scopus.com/inward/record.url?scp=37049083845&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049083845&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:37049083845

SP - 1131

EP - 1137

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

SN - 1472-7781

IS - 9

ER -