Total Synthesis of (8S) and (8R) Methyl 8-β-d-Glucopyranosyl-Helianthenate B and Their Application for Other Derivatives-Reference-Cited by-同舟云学术

Total Synthesis of (8S) and (8R) Methyl 8-β-d-Glucopyranosyl-Helianthenate B and Their Application for Other Derivatives

Published:2019-07 Issue:7 Volume:14 Page:1934578X1986101
ISSN:1934-578X
Container-title:Natural Product Communications
language:en
Short-container-title:Natural Product Communications

Author:

Masimbula Rishni¹,Yamada Akiko¹,Takahashi Kosaku²,Matsuura Hideyuki¹

Affiliation:

1. Laboratory of Natural Product Chemistry, Division of Fundamental AgriScience Research, Research Faculty of Agriculture, Hokkaido University, Sapporo, Japan

2. Department of Nutritional Science, Faculty of Applied Bioscience, Tokyo University of Agriculture, Setagaya-ku, Japan

Abstract

The first total synthesis of (8 R) and (8 S) methyl β-d-glucopyranosyl helianthenate B was accomplished using the Cadiot-Chodkiewicz coupling reaction as a key step. Significant differences were observed in the resonances between the 1H-NMR and 13C-NMR spectra of the diastereomers. Based on these results, the absolute configurations of glucopyranosyloxymethine in methyl β-d-glucopyranosyl helianthenate A to E (1 -5) were reconfirmed to be the ( R) configuration.

Publisher

SAGE Publications

Subject

Complementary and alternative medicine,Plant Science,Drug Discovery,Pharmacology,General Medicine

Link

http://journals.sagepub.com/doi/pdf/10.1177/1934578X19861013

Reference3 articles.

1. Tuber-forming Substances in Jerusalem Artichoke (Helianthus tuberosusL.)

2. Four New Polyacetylenic Glucosides, Methylβ-D-Glucopyranosyl Helianthenate C-F, from Jerusalem Artichoke(Helianthus tuberosusL.)

3. 144. Chemistry of the higher fungi. Part X. Further polyacetylenic derivatives of decane from various basidiomycetes

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