Total synthesis of the macrolactone AKML-B

被引：0
作者：
Kesavulu, Gangarajulu [1 ]
Silambarasan, Kanniyappan [1 ]
Prasad, Kavirayani R. [1 ]
机构：
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, India
来源：
TETRAHEDRON | 2024年 / 166卷
关键词：
KINETIC RESOLUTION; 2-FURYLCARBINOLS; HYDROGENATION; ACID;
D O I：
10.1016/j.tet.2024.134205
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Total synthesis of the 24-memebred macrolactone AKML-B was accomplished starting from a chiral furyl carbinol. The key reaction in the present approach includes the oxidation of furan to an unsaturated keto aldehyde and the use of Ring Closing Metathesis (RCM) reaction for the macrolactone formation.
引用
收藏
页数：10
相关论文
共 17 条
  • [1] Furan Oxidation Strategy for the Synthesis of the Macrolactone Analogue of Migrastatin
    Airan, Yougant
    Prasad, Kavirayani R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (22) : 14974 - 14979
  • [2] Total synthesis of (-)-(3R,6S,9R)-decarestrictine C2
    Arai, M
    Morita, N
    Aoyagi, S
    Kibayashi, C
    [J]. TETRAHEDRON LETTERS, 2000, 41 (08) : 1199 - 1203
  • [3] Enantiospecific Total Synthesis of Macrolactone Sch 725674
    Bali, Amit K.
    Sunnam, Sunil K.
    Prasad, Kavirayani R.
    [J]. ORGANIC LETTERS, 2014, 16 (15) : 4001 - 4003
  • [4] Sulfinyl-Mediated Stereoselective Functionalization of Acyclic Conjugated Dienes
    Colomer, Ignacio
    Urena, Mercedes
    Viso, Alma
    Fernandez de la Pradilla, Roberto
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (20) : 4620 - 4632
  • [5] Synthesis and Biological Evaluation of Highly Potent Fungicidal Deoxy-Hygrophorones
    Ditfe, Toni
    Bette, Eileen
    Sultani, Haider N.
    Otto, Alexander
    Wessjohann, Ludger A.
    Arnold, Norbert
    Westermann, Bernhard
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (27) : 3827 - 3836
  • [6] Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture
    Fujii, A
    Hashiguchi, S
    Uematsu, N
    Ikariya, T
    Noyori, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) : 2521 - 2522
  • [7] KINETIC RESOLUTION OF 2-FURYLCARBINOLS USING THE SHARPLESS OXIDATION AND ITS APPLICATION TO THE SYNTHESIS OF (5R,6S)-6-ACETOXY-5-HEXADECANOLIDE
    KAMETANI, T
    TSUBUKI, M
    TATSUZAKI, Y
    HONDA, T
    [J]. HETEROCYCLES, 1988, 27 (09) : 2107 - 2110
  • [8] Efficient conditions for conversion of 2-substituted furans into 4-oxygenated 2-enoic acids and its application to synthesis of (+)-aspicilin, (+)-patulolide A, and (-)-pyrenophorin
    Kobayashi, Y
    Nakano, M
    Kumar, GB
    Kishihara, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) : 7505 - 7515
  • [9] PREPARATION OF OPTICALLY-ACTIVE 2-FURYLCARBINOLS BY KINETIC RESOLUTION USING THE SHARPLESS REAGENT AND THEIR APPLICATION IN ORGANIC-SYNTHESIS
    KUSAKABE, M
    KITANO, Y
    KOBAYASHI, Y
    SATO, F
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (09) : 2085 - 2091
  • [10] LANTHANIDES IN ORGANIC-CHEMISTRY .1. SELECTIVE 1,2 REDUCTIONS OF CONJUGATED KETONES
    LUCHE, JL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (07) : 2226 - 2227
12