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

被引：23
作者：
Cen-Pacheco, Francisco [1 ]
Mollinedo, Faustino [2 ]
Villa-Pulgarin, Janny A. [2 ,3 ]
Norte, Manuel [1 ,4 ]
Fernandez, Jose J. [1 ,4 ]
Hernandez Daranas, Antonio [1 ,5 ]
机构：
[1] Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, E-38206 Tenerife, Spain
[2] Univ Salamanca, CSIC, Ctr Invest Canc, Inst Biol Mol & Celular Canc, E-37007 Salamanca, Spain
[3] Univ Salamanca, APOINTECH, Ctr Hispanoluso Invest Agr, E-37185 Salamanca, Spain
[4] Univ La Laguna, Dept Quim Organ, E-38206 Tenerife, Spain
[5] Univ La Laguna, Dept Ingn Quim & Tecnol Farmaceut, E-38206 Tenerife, Spain
来源：
TETRAHEDRON | 2012年 / 68卷 / 36期
关键词：
Marine natural products; Laurencia; Marine polyether; NMR spectroscopy; Chemical synthesis; MARINE NATURAL-PRODUCTS; TRITERPENE POLYETHERS;
D O I：
10.1016/j.tet.2012.07.005
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7275 / 7279
页数：5
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