A Stereoselective Total Synthesis of Xyolide, a Natural Bioactive Nonenolide

被引：3
|
作者：
Maram, Lingaiah [1 ]
Das, Biswanath [1 ]
机构：
[1] CSIR Indian Inst Chem Technol, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India
来源：
HELVETICA CHIMICA ACTA | 2015年 / 98卷 / 05期
关键词：
Nonenolide; Xyolide; Stereoselective syntheses; (2Z)-But-2-ene-1; 4-diol; D-Mannitol; FORMAL TOTAL-SYNTHESIS; PHYTOTOXIC NONENOLIDE; STAGONOSPORA-CIRSII; METATHESIS; ORIGIN;
D O I：
10.1002/hlca.201400291
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A stereoselective total synthesis of xyolide, a naturally occurring bioactive nonenolide, has been accomplished. The acid fragment of the molecule has been prepared from D-mannitol and the alcohol fragment from (2Z)-but-2-ene-1,4-diol. The synthesis involves the coupling of these two fragments using the Yamaguchi esterification protocol, followed by intramolecular ring-closing methathesis. The diastereoisomeric alcohol fragment has also been utilized in this synthesis by employing the Mitsunobu esterification.
引用
收藏
页码：674 / 682
页数：9
相关论文
共 50 条
  • [41] Stereoselective total synthesis of (+)-norrisolide
    Brady, TP
    Kim, SH
    Wen, K
    Theodorakis, EA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (06) : 739 - 742
  • [42] A STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-OXYLUBIMIN
    IWATA, C
    TAKEMOTO, Y
    KUBOTA, H
    KURODA, T
    IMANISHI, T
    TETRAHEDRON LETTERS, 1985, 26 (27) : 3231 - 3234
  • [43] Stereoselective total synthesis of (−)-pyrenophorol
    Dongamanti Ashok
    Sridhar Pervaram
    Venkata Ramana Reddy Chittireddy
    Sreenivasulu Reddymasu
    Naresh Kumar Vuppula
    Chemical Papers, 2018, 72 : 971 - 977
  • [44] STEREOSELECTIVE TOTAL SYNTHESIS OF (+-)-SEYCHELLENE
    PIERS, E
    BRITTON, RW
    DEWAAL, W
    JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (18): : 1069 - &
  • [45] Stereoselective total synthesis of muconin
    Takahashi, S
    Kubota, A
    Nakata, T
    TETRAHEDRON, 2003, 59 (10) : 1627 - 1638
  • [46] STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-ZIZAENE
    COATES, RM
    SOWERBY, RL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (15) : 5386 - &
  • [47] Stereoselective Total Synthesis of Rugulactone
    Das, Biswanath
    Srinivas, Yallamalla
    Sudhakar, Chithaluri
    Reddy, Parigi Raghavendar
    HELVETICA CHIMICA ACTA, 2011, 94 (07) : 1290 - 1295
  • [48] Stereoselective total synthesis of (-)-pyrenophorol
    Yadav, J. S.
    Reddy, U. V. Subba
    Reddy, B. V. Subba
    TETRAHEDRON LETTERS, 2009, 50 (44) : 5984 - 5986
  • [49] Stereoselective total synthesis of(-)-deoxoprosophylline
    Datta, A
    Kumar, JSR
    Roy, S
    TETRAHEDRON, 2001, 57 (07) : 1169 - 1173
  • [50] Stereoselective Total Synthesis of Carolacton
    Kuilya, Tapan Kumar
    Goswami, Rajib Kumar
    ORGANIC LETTERS, 2017, 19 (09) : 2366 - 2369
12345