Saiyacenols A and B: the key to solve the controversy about the configuration of aplysiols

Two new cytotoxic oxasqualenoids, saiyacenols A and B, were isolated from the red alga Laurencia viridis and their structures elucidated by spectroscopic methods and chemical correlation with the well-known compound dehydrothyrsiferol. The new compounds share an important part of their structure wit...

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Bibliographic Details
Published in:Tetrahedron 2012-09, Vol.68 (36), p.7275-7279
Main Authors: Cen-Pacheco, Francisco, Mollinedo, Faustino, Villa-Pulgarín, Janny A., Norte, Manuel, Fernández, José J., Hernández Daranas, Antonio
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Carbon
Chemical synthesis
Chemistry
Correlation
Demand
Exact sciences and technology
Laurencia
Marine natural products
Marine polyether
NMR spectroscopy
Nuclear magnetic resonance
Organic chemistry
Preparations and properties
Proposals
Spectroscopy
Terpenoids
Tetrahedrons
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Summary:Two new cytotoxic oxasqualenoids, saiyacenols A and B, were isolated from the red alga Laurencia viridis and their structures elucidated by spectroscopic methods and chemical correlation with the well-known compound dehydrothyrsiferol. The new compounds share an important part of their structure with thyrsiferol and aplysiols B and C. Isolation of the saiyacenols concludes the controversy about the configuration of aplysiols, correcting the structure of aplysiol B. Our results illustrate the current limitations of NMR J-based methods when approaching quaternary carbons and demand a reappraisal of rational biogenetic proposals in structural elucidation. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.07.005