The Total Synthesis and Structural Assignment of Hexaketide XylarinolB and its C1-Epimer

被引：10
|
作者：
Mullapudi, Venkannababu [1 ]
Ramana, Chepuri V. [1 ]
机构：
[1] CSIR, Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 5卷 / 03期
关键词：
2+2+2]-cyclotrimerization; hexaketides; sordarial; Wilkinson's catalyst; xylarinolB; CATALYZED 2+2+2 CYCLOADDITION; FORMAL TOTAL-SYNTHESIS; CONSTRUCTION; CYCLIZATIONS; METABOLITES; DERIVATIVES; COMPLEXES; SORDARIOL; DIYNES; ALKYNE;
D O I：
10.1002/ajoc.201500511
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of two isomeric hexaketides isolated along with sordarial, which have the proposed relative arabino and ribo configurations, has been executed. A Rh-catalyzed [2+2+2]-alkyne cyclotrimerization has been employed as the key reaction to construct the central dihydroisobenzofuran core. The absolute configuration of the xylarinolB hexaketide has been established as l-arabino. This is the first natural product of this family for which the absolute configuration has been determined, and this can be extended to provide structural details of several of related hexaketides.
引用
收藏
页码：417 / 422
页数：6
相关论文
共 50 条
  • [1] Total synthesis of (±) carbocyclic polyoxin C and its α-epimer
    Zhang, DY
    Miller, MJ
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03): : 755 - 759
  • [2] Total Synthesis of Thiocladospolide A and Its C2-Epimer
    Swami, Pramod
    Mali, Maruti
    Dhulshette, Baswaraj
    Ghosh, Subhash
    Synthesis (Germany), 2021, 54 (03) : 683 - 688
  • [3] Total Synthesis of Thiocladospolide A and Its C2-Epimer
    Swami, Pramod
    Mali, Maruti
    Dhulshette, Baswaraj
    Ghosh, Subhash
    SYNTHESIS-STUTTGART, 2022, 54 (03): : 683 - 688
  • [4] TOTAL SYNTHESIS OF NEOCLAUSENAMIDE AND ITS EPIMER
    Dao Fei HUANG
    Han Sen LIN and Liang HUANG (Inshtute of Materia Medica
    Chinese Chemical Letters, 1994, (05) : 371 - 372
  • [5] Total Synthesis and Structural Assignment of Curvicollide C
    von Kiedrowski, Valeska
    Quentin, Florian
    Hiersemann, Martin
    ORGANIC LETTERS, 2017, 19 (16) : 4391 - 4394
  • [6] First total synthesis of Pestalotioprolide C and its C7 epimer
    Reddy, K. Siva Nagi
    Sabitha, Gowravaram
    TETRAHEDRON LETTERS, 2017, 58 (12) : 1198 - 1201
  • [7] First total synthesis of parvistone C and its C8-epimer
    Jala, Ranjith
    Nomula, Rajesh
    Krishna, Palakodety Radha
    SYNTHETIC COMMUNICATIONS, 2017, 47 (20) : 1879 - 1883
  • [8] Total synthesis of (±)-nakamurol-A and its 13-epimer:: tentative assignment of the C-13 relative configuration
    Bonjoch, J
    Cuesta, J
    Díaz, S
    González, A
    TETRAHEDRON LETTERS, 2000, 41 (30) : 5669 - 5672
  • [9] Total synthesis of lycoperdic acid and its C4-epimer
    Morokuma, Kenji
    Irie, Raku
    Oikawa, Masato
    TETRAHEDRON LETTERS, 2019, 60 (31) : 2067 - 2069
  • [10] Total synthesis of natural (+)-membrenone C and its 7-epimer
    Yadav, JS
    Srinivas, R
    Sathaiah, K
    TETRAHEDRON LETTERS, 2006, 47 (10) : 1603 - 1606
12345