STEREOCHEMICAL ASSIGNMENT AT C-24 AND C-25 OF MARINE 24-ETHYL-26-HYDROXY STEROIDS THROUGH COMPARISON WITH SYNTHETIC (24S,25S)-MODELS, (24S,25R)-MODELS, (24R,25R)-MODELS, AND (24R,25S)-MODELS

被引:7
作者
DAURIA, MV [1 ]
PALOMA, LG [1 ]
MINALE, L [1 ]
RICCIO, R [1 ]
机构
[1] UNIV NAPOLI FEDERICO 2,DIPARTIMENTO CHIM SOSTANZE NAT,VIA D MONTESANO 49,I-80131 NAPLES,ITALY
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 11期
关键词
D O I
10.1039/p19900002895
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereoisomeric Δ22E-24-ethyl-26-hydroxy steroids (7a), (7b), (8a), and (8b) and the corresponding 22,23-dihydro derivatives (9a), (9b), (l0a), and (10b) were synthesized. Analysis of 1H and 13C NMR spectra of the synthetic model compounds and of their MTPA derivatives provided data suitable for the assignment of configuration at C-24 and C-25 in 24-ethyl-26-hydroxy steroids. From those models and the related spectral data, the stereochemistry (24S,25S) has been assigned to 24-ethyl-5- cholestane3α,4α,21,26-tetraol 3,21 -disulphate, recently isolated from the marine ophiuroid Ophiolepis superba.
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页码:2895 / 2898
页数:4
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