Synthesis and revision of stereochemistry of rubescensin S

Mei Zhang; Yangming Zhang; Wei Lu; Fa-Jun Nan

doi:10.1039/c1ob05611e

Synthesis and revision of stereochemistry of rubescensin S

Org Biomol Chem. 2011 Jun 21;9(12):4436-9. doi: 10.1039/c1ob05611e. Epub 2011 May 16.

Authors

Mei Zhang¹, Yangming Zhang, Wei Lu, Fa-Jun Nan

Affiliation

¹ Department of Chemistry and Institute of Medicinal Chemistry, East China Normal University, 3663 North Zhong Shan Road, Shanghai, 200062, China.

PMID: 21584305
DOI: 10.1039/c1ob05611e

Abstract

An effective two step transformation of oridonin to 15,16-seco-ent-kaurane skeleton is reported. We also achieved the conversion of one intermediate to natural product rubescensin S and revised its structure as a 13S configuration although 13R is reported in the literature.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / chemical synthesis*
Antineoplastic Agents, Phytogenic / pharmacology
Cell Survival / drug effects
Chemistry, Pharmaceutical / methods*
Crystallography, X-Ray
Diterpenes, Kaurane / chemical synthesis*
Diterpenes, Kaurane / pharmacology
Drugs, Chinese Herbal / chemical synthesis*
Drugs, Chinese Herbal / pharmacology
Humans
Inhibitory Concentration 50
Isodon / chemistry
K562 Cells
Magnetic Resonance Spectroscopy
Molecular Structure
Small Molecule Libraries / chemical synthesis
Stereoisomerism

Substances

Antineoplastic Agents, Phytogenic
Diterpenes, Kaurane
Drugs, Chinese Herbal
Small Molecule Libraries
rubescensin S
oridonin