A Straightforward Synthesis of Emericellamide A Using Matteson's Homologation Approach

被引:2
|
作者
Priester, Ronja [1 ]
Kazmaier, Uli [1 ]
机构
[1] Saarland Univ, Organ Chem, D-66123 Saarbrucken, Germany
关键词
boronic esters; Matteson homologation; natural products; peptides; stereoselective synthesis; ANTI-ALDOL REACTIONS; BORONIC ESTERS; STEREOSELECTIVE-SYNTHESIS; BIOLOGICAL EVALUATION; ASYMMETRIC-SYNTHESIS; ESTERIFICATION; SELECTIVITY;
D O I
10.1055/a-2077-2113
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Matteson homologation is the perfect approach for the synthesis of polyketide-peptide natural products such as the emericellamides. In only four steps, the polyketide fragment with three stereo genic centers can be obtained as a single stereoisomer. The peptide fragment is easily available via solid-phase peptide synthesis.
引用
收藏
页码:2159 / 2164
页数:6
相关论文
共 50 条
  • [41] Hydrazinosulfonylation of aryl electrophiles: a straightforward approach for the synthesis of aryl N-aminosulfonamides
    Hsu, Chou-Yi
    Aldulaimi, Ahmed Kareem Obaid
    Sami, Mustafa Humam
    Bahir, Hala
    Adhab, Ayat Hussein
    Saraswat, Shelesh Krishna
    RSC ADVANCES, 2023, 13 (27) : 18546 - 18560
  • [42] A Straightforward Synthesis of a-Amino Phosphonate Monoesters Using BroP or TPyClU
    Galeotti, N.
    Coste, J.
    Bedos, P.
    Jouin, P.
    Tetrahedron Letters, 37 (23):
  • [43] Catalytic asymmetric synthesis of hydroxy enol ethers: Approach to a two-carbon homologation of aldehydes
    Jeon, SJ
    Chen, YK
    Walsh, PJ
    ORGANIC LETTERS, 2005, 7 (09) : 1729 - 1732
  • [44] A Straightforward Approach to Eringen's Nonlocal Elasticity Stress Model and Applications for Nanobeams
    Koutsoumaris, C. Chr.
    Eptaimeros, K. G.
    Zisis, T.
    Tsamasphyros, G. J.
    PROCEEDINGS OF THE INTERNATIONAL CONFERENCE OF COMPUTATIONAL METHODS IN SCIENCES AND ENGINEERING 2016 (ICCMSE-2016), 2016, 1790
  • [45] Ru(0)-Catalyzed Straightforward Synthesis of Conjugated Tetraenes: An Approach using Two Internal Alkynes with 1,3-Butadiene
    Kiyota, Sayori
    Hirano, Masafumi
    ORGANOMETALLICS, 2018, 37 (02) : 227 - 234
  • [46] Efficient synthesis of ethanol by methanol homologation using CO2 at lower temperature
    Wang, Ying
    Zhang, Jingjing
    Qian, Qingli
    Bediako, Bernard Baffour Asare
    Cui, Meng
    Yang, Guanying
    Yan, Jiang
    Han, Buxing
    GREEN CHEMISTRY, 2019, 21 (03) : 589 - 596
  • [47] Aryne polymerization enabling straightforward synthesis of elusive poly(ortho -arylene)s
    Mikami, Koichiro (koichiro.mikami@riken.jp), 1600, American Chemical Society (137):
  • [48] 1ST TOTAL SYNTHESIS OF THE INDOLE ALKALOID ERVITSINE - A STRAIGHTFORWARD, BIOMIMETIC APPROACH
    BENNASAR, ML
    VIDAL, B
    BOSCH, J
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) : 5340 - 5341
  • [49] Bisindoles. 41*. a straightforward approach towards the synthesis of new bis-pyridazinoindoles
    A. Z. Kalatozishvili
    N. Sh. Samsonia
    N. L. Targamadze
    I. Sh. Chikvaidze
    Sh. A. Samsoniya
    A. O. Wesquet
    Uli Kazmaier
    Chemistry of Heterocyclic Compounds, 2010, 46 : 608 - 612
  • [50] Regioselective preparation of tetrasubstituted alkenes from ketones using Krief's methodology as a key step for a straightforward synthesis of dienynes
    Petit, Marc
    Chouraqui, Gaelle
    Aubert, Corinne
    Malacria, Max
    ARKIVOC, 2007, : 278 - 291