Stereoselective synthesis of an advanced seco ester intermediate as a precursor toward the synthesis of amphidinolides T1, T3, and T4

被引:8
作者
Sasmal, Pradip K. [1 ]
Abbineni, Chandrasekhar [1 ,2 ]
Iqbal, Javed [1 ,3 ]
Mukkanti, K. [2 ]
机构
[1] Dr Reddys Labs Ltd, Discovery Res, Hyderabad 500049, Andhra Pradesh, India
[2] JNT Univ, Inst Sci & Technol, Div Chem, Hyderabad 500072, Andhra Pradesh, India
[3] Inst Life Sci, Hyderabad 500046, Andhra Pradesh, India
关键词
Amphidinolide T family; Evan's aldol; Evan's alkylation; Oxy-Michael; Cross metathesis; CBS reduction; ENANTIOSELECTIVE SYNTHESIS; 19-MEMBERED MACROLIDE; DINOFLAGELLATE; ACID; COMPLEXES; ALCOHOLS; FRAGMENT; T2;
D O I
10.1016/j.tet.2010.05.012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, convergent, and stereoselective synthesis of a very advanced intermediate toward the total synthesis of amphidinolides T1, T3, and T4 utilising Evan's aldol and alkylation reactions, oxy-Michael, cross metathesis, stereoselective Grignard addition, and Yamaguchi esterification reactions as key steps is described. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5000 / 5007
页数:8
相关论文
共 44 条
  • [1] Synthesis of the C1-C12 fragment of amphidinolide T1
    Abbineni, Chandrasekhar
    Sasmal, Pradip K.
    Mukkanti, K.
    Iqbal, Javed
    [J]. TETRAHEDRON LETTERS, 2007, 48 (24) : 4259 - 4262
  • [2] Ruthenium carbene complexes with imidazolin-2-ylidene ligands allow the formation of tetrasubstituted cycloalkenes by RCM
    Ackermann, L
    Fürstner, A
    Weskamp, T
    Kohl, FJ
    Herrmann, WA
    [J]. TETRAHEDRON LETTERS, 1999, 40 (26) : 4787 - 4790
  • [3] Total syntheses of amphidinolide T1, T3, T4, and T5
    Aïssa, C
    Riveiros, R
    Ragot, J
    Fürstner, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (50) : 15512 - 15520
  • [4] Chakraborty Tushar K., 2001, Current Medicinal Chemistry - Anti-Cancer Agents, V1, P131, DOI 10.2174/1568011013354660
  • [5] A general model for selectivity in olefin cross metathesis
    Chatterjee, AK
    Choi, TL
    Sanders, DP
    Grubbs, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) : 11360 - 11370
  • [6] Total syntheses of amphidinolides T1 and T4 via catalytic, stereoselective, reductive macrocyclizations
    Colby, EA
    O'Brien, KC
    Jamison, TF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) : 4297 - 4307
  • [7] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS
    COREY, EJ
    BAKSHI, RK
    SHIBATA, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) : 5551 - 5553
  • [8] Asymmetric aldol additions:: Use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones
    Crimmins, MT
    King, BW
    Tabet, EA
    Chaudhary, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) : 894 - 902
  • [9] An improved synthetic preparation of 3-butenal
    Crimmins, MT
    Kirincich, SJ
    Wells, AJ
    Choy, AL
    [J]. SYNTHETIC COMMUNICATIONS, 1998, 28 (19) : 3675 - 3679
  • [10] Stereocontrolled and convergent total synthesis of amphidinolide T3
    Deng, Li-Sheng
    Huang, Xiao-Ping
    Zhao, Gang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (12) : 4625 - 4635