Total Synthesis of (3R, 4S)-4-Hydroxylasiodiplodin via Ring Closing Metathesis Protocol

被引:5
|
作者
Reddy, Julakanti Satyanarayana [1 ]
Manimala, Patel [1 ]
Gangababu, Marri [1 ]
Rammohan, Aluru [1 ,2 ]
Yadav, Jillu Singh [1 ]
机构
[1] CSIR, Indian Inst Chem Technol, Ctr Semiochem, Hyderabad 500007, Telangana, India
[2] Sri Venkateswara Univ, Dept Chem, Tirupati 517502, Andhra Pradesh, India
来源
CHEMISTRYSELECT | 2019年 / 4卷 / 18期
关键词
D-isoascorbic acid; Lasiodiplodin; Mitsunobu reaction; Regioselective ring opening; Ring-Closing Metathesis; FACILE TOTAL-SYNTHESIS; LASIODIPLODIN; CHEMISTRY; LACTONES;
D O I
10.1002/slct.201900189
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Total synthesis of (3R, 4S)-4-Hydroxylasiodiplodin has been accomplished through convergent strategy using D-isoascorbic acid and trihydroxybenzoic acid as the starting materials in an optimal reaction sequence. The salient features of the synthesis are the utilization of Stille coupling, trans-esterification and Ring-Closing Metathesis (RCM).
引用
收藏
页码:5345 / 5347
页数:3
相关论文
共 50 条
  • [21] A novel, facile and diastereoselective synthesis of (3S, 4S) and (3R, 4S)-N-Me-AHPPA
    Reddy, GV
    Rao, GV
    Iyengar, DS
    CHEMISTRY LETTERS, 1999, (07) : 703 - 704
  • [22] A concise total synthesis of dactylol via ring closing metathesis
    Furstner, A
    Langemann, K
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25): : 8746 - 8749
  • [23] STEREOSELECTIVE SYNTHESIS OF (3R, 4S)-N-BOC-STATINE
    SAVRDA, J
    DESCOINS, C
    SYNTHETIC COMMUNICATIONS, 1987, 17 (16) : 1901 - 1906
  • [24] Asymmetric syntheses of (1r,3R,4S)- and (1s,3R,4S)-(3,4-difluorocyclopentyl)-alanine derivatives
    Simpson, Robert D.
    Zhao, Wei
    TETRAHEDRON-ASYMMETRY, 2009, 20 (13) : 1515 - 1520
  • [25] Diastereoselective Syntheses of (3R*,4R*)- and (3R*,4S*)-4-Aryl-3-methyl-4-piperidinemethanol and Fluoro Analogues
    Schmitt, Sebastien
    Brown, Richard C. D.
    Perrio, Cecile
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (03): : 1222 - 1229
  • [26] Synthesis of Novel Calix[4]arenocrowns via Ring-closing Metathesis
    Lu Lin-Gang
    Lue Hai-Yan
    CHINESE JOURNAL OF CHEMISTRY, 2008, 26 (10) : 1759 - 1763
  • [27] Total synthesis of (S)-(+)-citreofuran by ring closing alkyne metathesis
    Fürstner, A
    Castanet, AS
    Radkowski, K
    Lehmann, CW
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04): : 1521 - 1528
  • [28] Chemoenzymatic synthesis of orthogonally protected (3R,4R)- and (3S,4S)-trans-3-amino-4-hydroxypyrrolidines
    Rodriguez-Rodriguez, Jesus A.
    Javier Quijada, F.
    Brieva, Rosario
    Rebolledo, Francisca
    Gotor, Vicente
    TETRAHEDRON, 2013, 69 (26) : 5407 - 5412
  • [29] A concise stereoselective total synthesis of (2R,2′R)-threo-(+)-methylphenidate via a ring-closing metathesis protocol
    Krishna, Palakodety Radha
    Lopinti, Krishnarao
    SYNLETT, 2007, (11) : 1742 - 1744
  • [30] Total synthesis of octalactin A via ring-closing metathesis.
    Buszek, KR
    Sato, N
    Jeong, Y
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U54 - U54