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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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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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creator	Cen-Pacheco, Francisco Mollinedo, Faustino Villa-Pulgarín, Janny A. Norte, Manuel Fernández, José J. Hernández Daranas, Antonio
description	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]
doi_str_mv	10.1016/j.tet.2012.07.005
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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
title	Saiyacenols A and B: the key to solve the controversy about the configuration of aplysiols
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