Design and synthesis of a simplified analogue of salacinol
- VernacularTitle:Salacinol结构类似简化物的设计与合成
- Author:
Ying SHAO
;
Muraoka OSAMU
;
Tanabe GENZOH
;
Gotoh HIROYOSHI
;
Qidong YOU
- Publication Type:Journal Article
- Keywords:
salacinol;
analogue;
sulfonium salt;
S-alkylation;
O-sulfonilation
- From:
Journal of China Pharmaceutical University
2006;(5):403-406
- CountryChina
- Language:Chinese
-
Abstract:
To investigate a key strategy of the total synthesis of salacinol. Methods: A simplified analogue of salacinol (1),1-(3-sulfooxypropyl)tetrahydrothiophenium inner salt (2) was designed and synthesized by a coupling reaction between tetrahydrothiophene (THT) and 3-iodopropanol (3-IPA) followed by the esterification of the resulting sulfonium with sulfur trioxide pyridine complex (SO3*Py). Replacement of the alkylating reagent (3-IPA) of THT led to the predominate formation of a undesirable cyclic compound,2,2-dioxo-1,3,2-dioxathiane (7). Resutls:This model experiments indicated that the tandem synthetic process leading to the sulfonium sulfate 2 could be applied for the total synthesis of salacinol (1) as an alternative method.
