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
相关论文
共 50 条
  • [21] Total syntheses of kealiinines A-C along with kealiiquinone and 2-deoxy-2-aminokealiiquinone
    Das, Jayanta K.
    Lovely, Carl J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [22] Final-Stage Site-Selective Acylation for the Total Syntheses of Multifidosides A-C
    Ueda, Yoshihiro
    Furuta, Takumi
    Kawabata, Takeo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (41) : 11966 - 11970
  • [23] Total synthesis and comparative evaluation of luzopeptin A-C and quinoxapeptin A-C
    Boger, DL
    Ledeboer, MW
    Kume, M
    Searcey, M
    Jin, Q
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) : 11375 - 11383
  • [24] Total Synthesis of Glycinocins A-C
    Corcilius, Leo
    Elias, Nabiha T.
    Ochoa, Jessica L.
    Linington, Roger G.
    Payne, Richard J.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23): : 12778 - 12785
  • [25] Total synthesis of amphemedosides A-C
    Langenhan, Joseph M.
    Rohlfing, James
    Rogalsky, Derek
    Tjaden, Anja
    Werner, Halina
    Mullarky, Edouard
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [26] Total Synthesis of Chaetoquadrins A-C
    Kim, U. Bin
    Furkert, Daniel P.
    Brimble, Margaret A.
    ORGANIC LETTERS, 2013, 15 (03) : 658 - 661
  • [27] Total synthesis of luzopeptins A-C
    Boger, DL
    Ledeboer, MW
    Kume, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) : 1098 - 1099
  • [28] Total synthesis of marinomycins A-C
    Nicolaou, K. C.
    Nold, Andrea L.
    Milburn, Robert R.
    Schindler, Corinna S.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) : 6527 - 6532
  • [29] Total synthesis of luzopeptins A-C
    J Am Chem Soc, 5 (1098):
  • [30] Unified Total Syntheses of (±)-Sessilifoliamides B, C, and D
    Olivier, Wesley J.
    Bissember, Alex C.
    Smith, Jason A.
    ORGANIC LETTERS, 2021, 23 (09) : 3437 - 3441
12345