Epoxide Opening of a 7,17-Seco–7,8-Epoxy-C19-Diterpenoid Alkaloid-Reference-Cited by-同舟云学术

Epoxide Opening of a 7,17-Seco–7,8-Epoxy-C19-Diterpenoid Alkaloid

Published:2015-12 Issue:12 Volume:10 Page:1934578X1501001
ISSN:1934-578X
Container-title:Natural Product Communications
language:en
Short-container-title:Natural Product Communications

Author:

Ji Hong¹,Wang Feng-Peng²,Chen Qiao-Hong³

Affiliation:

1. Pharmaceutical Research Center, School of Pharmaceutical Science, Guangzhou Medical University, Guangzhou, Guangdong 511436, China

2. Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu, Sichuan 610041, China

3. Department of Chemistry, California State University, Fresno, 2555 E. San Ramon Ave. M/S SB70, Fresno, California USA 93740

Abstract

A new and effective approach toward epoxide opening of a 7,17- seco–7,8-epoxy-C19-diterpenoid alkaloid is herein described. The starting epoxide was prepared from naturally occurring yunnaconitine via a nine-step transformation. Treatment of this epoxide with trifluoroacetic anhydride in dioxane at 110oC followed by reduction with sodium boron hydride generated two epoxide opening compounds 7 and 8. Each of their structures is characteristic of a Δ8,15 bridgehead double bond and a 7β-oxygen-substituted group.

Publisher

SAGE Publications

Subject

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

Link

http://journals.sagepub.com/doi/pdf/10.1177/1934578X1501001215

Reference14 articles.

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5. To seek an approach toward the chemical conversion of C19-diterpenoid alkaloids to taxoids