Absolute Configuration and Conformational Study of Psammaplysins A and B from the Balinese Marine Sponge Aplysinella strongylata

被引:67
|
作者
Mandi, Attila [1 ]
Mudianta, I. Wayan [2 ,3 ]
Kurtan, Tibor [1 ]
Garson, Mary J. [2 ]
机构
[1] Univ Debrecen, Dept Organ Chem, Debrecen, Hungary
[2] Univ Queensland, Sch Chem & Mol Biosci, Brisbane, Qld 4072, Australia
[3] Ganesha Univ Educ, Fac Math & Nat Sci, Dept Analyt Chem, Bali, Indonesia
来源
JOURNAL OF NATURAL PRODUCTS | 2015年 / 78卷 / 08期
基金
新加坡国家研究基金会;
关键词
VERONGIDA SPONGES; BROMOTYROSINE DERIVATIVES; CHEMISTRY; BROMOCOMPOUNDS;
D O I
10.1021/acs.jnatprod.5b00369
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The absolute configuration of psammaplysin A (1) has been assigned as (6R,7R) using experimental and calculated electronic circular dichroism (ECD) data and NMR analysis of MPA esters prepared from the acetamide derivative of 1. Detailed conformational analyses of a truncated model compound of 1 with an in vacuo method and with the PCM solvent model for MeOH have identified the major conformers and factors governing the ECD spectrum of 1. The correlation of the ECD data with the stereochemistry of 1 allows configurational assignment of related psammaplysin analogues on the basis of their ECD spectra.
引用
收藏
页码:2051 / 2056
页数:6
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