Enantioselective synthesis of polyketide segments through vinylogous Mukaiyama aldol reactions

被引:28
作者
Simsek, Serkan [1 ]
Kalesse, Markus [1 ]
机构
[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
关键词
Vinylogous Mukaiyama aldol; Polyketides; Oxazaborolidines; Natural products; Enantioselective; STEREOCONTROLLED TOTAL-SYNTHESIS; LEWIS-BASE ACTIVATION; NATURAL-PRODUCTS; ACIDS; ROFLAMYCOIN; ADDITIONS; CATALYST; COMPLEX;
D O I
10.1016/j.tetlet.2009.03.013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of polyketide segments through the vinylogous Mukaiyama aldol reaction is reported. The use of chiral oxazaborolidines allows using terminal substituted ketene acetals and provides access to extended segments and two new chiral centers. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3485 / 3488
页数:4
相关论文
共 39 条
  • [1] [Anonymous], 2005, Angew. Chem
  • [2] Toward the development of a general chiral auxiliary. Enantioselective alkylation and a new catalytic asymmetric addition of silyloxyfurans: Application to a total synthesis of (-)-rasfonin
    Boeckman, Robert K., Jr.
    Pero, Joseph E.
    Boehmler, Debra J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (34) : 11032 - 11033
  • [3] Highly Stereoselective Aldol Reactions in the Total Syntheses of Complex Natural Products
    Brodmann, Tobias
    Lorenz, Michael
    Schaeckel, Romy
    Simsek, Serkan
    Kalesse, Markus
    [J]. SYNLETT, 2009, (02) : 174 - 192
  • [4] The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver
    Casiraghi, G
    Zanardi, F
    Appendino, G
    Rassu, G
    [J]. CHEMICAL REVIEWS, 2000, 100 (06) : 1929 - 1972
  • [5] Christmann M, 2000, ANGEW CHEM INT EDIT, V39, P4364, DOI 10.1002/1521-3773(20001201)39:23<4364::AID-ANIE4364>3.0.CO
  • [6] 2-G
  • [7] Vinylogous Mukaiyama aldol reactions with triarylboranes
    Christmann, M
    Kalesse, M
    [J]. TETRAHEDRON LETTERS, 2001, 42 (07) : 1269 - 1271
  • [8] Christmann M., 2000, ANGEW CHEM, V112, P4535, DOI 10.1002/1521-3757(20001201)112:233.0.co
  • [9] 2-k
  • [10] Lewis base activation of lewis acids: Catalytic, enantioselective vinylogous aldol addition reactions
    Denmark, Scott E.
    Heemstra, John R., Jr.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15) : 5668 - 5688