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Scaparvin A, a novel caged cis-clerodane with an unprecedented C-6/C-11 bond, and related diterpenoids from the liverwort Scapania parva.

Authors
  • Guo, Dong-Xiao1
  • Zhu, Rong-Xiu
  • Wang, Xiao-Ning
  • Wang, Li-Ning
  • Wang, Shu-Qi
  • Lin, Zhao-Min
  • Lou, Hong-Xiang
  • 1 Department of Natural Products Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 West Wenhua Road, Jinan 250012, PR China. , (China)
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Oct 01, 2010
Volume
12
Issue
19
Pages
4404–4407
Identifiers
DOI: 10.1021/ol1019458
PMID: 20831228
Source
Medline
License
Unknown

Abstract

A novel caged cis-clerodane diterpenoid, scaparvin A, possessing an unprecedented C-6/C-11 bond and a ketal ring, as well as four new cis-clerodane derivatives, scaparvins B-E, were isolated from the Chinese liverwort Scapania parva. Their absolute structures were elucidated by analysis of NMR and CD data coupled with electronic circular dichroism (ECD) calculations. It was proposed that an enzymatic intramolecular aldol reaction was the key step in the biogenetic pathway of scaparvin A.

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