Total Syntheses of Rhodiolosides A and D and of Sachalinols A-C

被引：5
|
作者：
Simon, Kristina [1 ,2 ,3 ]
Jones, Peter G. [1 ,2 ,3 ]
Lindel, Thomas [1 ,2 ,3 ]
机构：
[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ, D-38106 Braunschweig, Germany
[2] Tech Univ Carolo Wilhelmina Braunschweig, Inst Inorgan, D-38106 Braunschweig, Germany
[3] Tech Univ Carolo Wilhelmina Braunschweig, Inst Analyt Chem, D-38106 Braunschweig, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 08期
关键词：
Glucosylation; Natural products; Rosiridol; Terpenoids; Oxygen heterocycles; Total synthesis; ABSOLUTE-CONFIGURATION; STEREOCHEMISTRY; MONOTERPENES; METABOLITES; ANALOGS;
D O I：
10.1002/ejoc.201001315
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The glucosylated monoterpenoids (-)-rhodioloside A and (-)-rhodioloside D from the roseroot (Rhodiola rosea) have been synthesized for the first time. Glucosylation with tetrapivaloylglucosyl bromide proved superior to the use of tetraacetylglucosyl bromide or glucosyl iodides. Acid-catalyzed cyclization of a homoglycidol-type geraniol derivative afforded the monoterpenoid tetrahydrofuran (+)-sachalinol C from Rhodiola sachalinensis. The absolute configuration of (+)-sachalinol C requires revision. (-)-Sachalinol A and (-)-sachalinol B were also obtained.
引用
收藏
页码：1493 / 1503
页数：11
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