Synthesis of 7-epi-Goniodiol by Proline-Catalyzed Diastereoselective Direct Aldol Reaction

被引：6
|
作者：
Veena, Bacchu [1 ]
Sharma, Gangavaram V. M. [1 ]
机构：
[1] Indian Inst Chem Technol, CSIR, Discovery Lab, Organ & Biomol Chem Div, Hyderabad 500007, Andhra Pradesh, India
来源：
SYNLETT | 2014年 / 25卷 / 09期
关键词：
styryllactones; 7-epi-goniodiol; proline; aldol reaction; Baeyer-Villiger oxidation; GONIOTHALAMIN; LACTONES;
D O I：
10.1055/s-0033-1341107
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple organocatalytic approach was developed for the total synthesis of 7-epi-goniodiol. The strategy involves l-proline-catalyzed diastereoselective direct aldol reaction and Baeyer-Villiger oxidation as key steps for the construction of chiral lactone.
引用
收藏
页码：1283 / 1286
页数：4
相关论文
共 50 条
  • [21] A revisit to proline-catalyzed aldol reaction: Interactions with acetone and catalytic mechanisms
    Yang, Gang
    Yang, Zhiwei
    Zhou, Lijun
    Zhu, Rongxiu
    Liu, Chengbu
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2010, 316 (1-2) : 112 - 117
  • [22] Theoretical study of the proline-catalyzed asymmetric intramolecular aldol reaction.
    Houk, KN
    Bahmanyar, S
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U218 - U218
  • [23] Switching Diastereoselectivity in Proline-Catalyzed Aldol Reactions
    Martinez-Castaneda, Angel
    Rodriguez-Solla, Humberto
    Concellon, Carmen
    del Amo, Vicente
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 10375 - 10381
  • [24] Proline-catalyzed asymmetric direct aldol reaction assisted by D-camphorsulfonic acid in aqueous media
    Wu, YS
    Chen, Y
    Deng, DS
    Cai, JW
    SYNLETT, 2005, (10) : 1627 - 1629
  • [25] DFT Study on the (S)-Proline-catalyzed Direct Aldol Reaction between Acetone and 4-Nitrobenzaldehyde
    樊建芬
    吴丽芬
    结构化学, 2006, (04) : 433 - 438
  • [26] DFT study on the (S)-proline-catalyzed direct aldol reaction between acetone and 4-nitrobenzaldehyde
    Fan, JF
    Wu, LF
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2006, 25 (04) : 433 - 438
  • [27] DFT Study on the (S)-Proline-catalyzed Direct Aldol Reaction between Acetone and 4-Nitrobenzaldehyde
    樊建芬
    吴丽芬
    Chinese Journal of Structural Chemistry, 2006, (04) : 433 - 438
  • [28] Origins of opposite absolute stereloselectivities in proline-catalyzed direct Mannich and aldol reactions
    Bahmanyar, S
    Houk, KN
    ORGANIC LETTERS, 2003, 5 (08) : 1249 - 1251
  • [29] Density functional theory study of the mechanism of the proline-catalyzed intermolecular aldol reaction
    Arnó, M
    Domingo, LR
    THEORETICAL CHEMISTRY ACCOUNTS, 2002, 108 (04) : 232 - 239
  • [30] Proline-catalyzed asymmetric aldol reaction in guanidine-derived ionic liquids
    Shah, Jabbar
    Blumenthal, Haiko
    Yacob, Zekarias
    Liebscher, Juergen
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) : 1267 - 1270
12345