Asymmetric synthesis and absolute stereochemistry of a labdane-type diterpenoid isolated from the rhizomes of Isodan yuennanensis-Reference-Cited by-同舟云学术

Asymmetric synthesis and absolute stereochemistry of a labdane-type diterpenoid isolated from the rhizomes of Isodan yuennanensis

Published:2016 Issue:26 Volume:14 Page:6225-6230
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Deng Heping¹²³⁴⁵,Cao Wei¹²³⁴⁵,Zhang Zhijiang¹²³⁴⁵,Liu Bo¹²³⁴⁵

Affiliation:

1. Key Laboratory of Green Chemistry & Technology of the Ministry of Education

2. College of Chemistry

3. Sichuan University

4. Chengdu

5. China

Abstract

Asymmetric synthesis of the title natural diterpenoid was achieved from (+)-sclareolide and its absolute configuration was determined accordingly. The synthesis includes inversion of chirality at C-8, remote functionalization directed by 8-OH, and oxidative lactonization.

Funder

China Pharmaceutical University

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2016/OB/C6OB00750C

Reference39 articles.

1. Furanoditerpenoids of the Labdane Series: Occurrence in Plants, Total Synthesis, Several Transformations, and Biological Activity

2. Use of (+)-manool in the Synthesis of Natural Products. Part II. Diterpenes and Relatives

3. Isolation, Chemical, and Biotransformation Routes of Labdane-type Diterpenes