Stereoselective Total Synthesis of Arundinolides A and B

被引：9
|
作者：
Chang, Caizhu [1 ,2 ]
Geng, Jialin [1 ,3 ]
Liu, Yinxin [1 ,3 ]
Du, Yuguo [1 ,3 ]
Liu, Jun [1 ,3 ]
Dong, Zhi-Bing [1 ,2 ]
机构：
[1] Chinese Acad Sci, Res Ctr Ecoenvironm Sci, State Key Lab Environm Chem & Ecotoxicol, Beijing 100085, Peoples R China
[2] Wuhan Inst Technol, Sch Chem & Environm Engn, Wuhan 430205, Peoples R China
[3] Univ Chinese Acad Sci, Sch Chem Sci, Beijing 100049, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2020年 / 52卷 / 10期
基金：
中国国家自然科学基金;
关键词：
arundinolides; total synthesis; chiral pool; regioselective reduction; crotonyl migration; ALPHA; BETA-UNSATURATED ESTERS; SECONDARY METABOLITES; SELECTIVE REDUCTION; ASPINOLIDE-B; ISOMERIZATION; TRICHODERMA;
D O I：
10.1055/s-0039-1691699
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The efficient and enantioselective syntheses of arundinolides A and B have been accomplished for the first time from chiral pool methyl-2,3-O-isopropylidene-beta-d-ribofuranoside and d-ethyl lactate. The key features of the total synthesis are intramolecular crotonyl migration and NaBH4-CuCl catalyzed regioselective reduction and cross-metathesis reaction.
引用
收藏
页码：1576 / 1584
页数：9
相关论文
共 50 条
  • [31] Stereoselective total synthesis of (+)-norrisolide
    Brady, TP
    Kim, SH
    Wen, K
    Theodorakis, EA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (06) : 739 - 742
  • [32] Stereoselective total synthesis of (−)-pyrenophorol
    Dongamanti Ashok
    Sridhar Pervaram
    Venkata Ramana Reddy Chittireddy
    Sreenivasulu Reddymasu
    Naresh Kumar Vuppula
    Chemical Papers, 2018, 72 : 971 - 977
  • [33] Stereoselective Total Synthesis of Carolacton
    Kuilya, Tapan Kumar
    Goswami, Rajib Kumar
    ORGANIC LETTERS, 2017, 19 (09) : 2366 - 2369
  • [34] Stereoselective total synthesis of (-)-borrelidin
    Vong, BG
    Kim, SH
    Abraham, S
    Theodorakis, EA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) : 3947 - 3951
  • [35] STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-ISHWARONE
    PIERS, E
    HALL, TW
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (23) : 880 - 881
  • [36] A STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-OXYLUBIMIN
    IWATA, C
    TAKEMOTO, Y
    KUBOTA, H
    KURODA, T
    IMANISHI, T
    TETRAHEDRON LETTERS, 1985, 26 (27) : 3231 - 3234
  • [37] Stereoselective total synthesis of(-)-deoxoprosophylline
    Datta, A
    Kumar, JSR
    Roy, S
    TETRAHEDRON, 2001, 57 (07) : 1169 - 1173
  • [38] STEREOSELECTIVE TOTAL SYNTHESIS OF (+-)-SEYCHELLENE
    PIERS, E
    BRITTON, RW
    DEWAAL, W
    JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (18): : 1069 - &
  • [39] The stereoselective total synthesis of (-)-achaetolide
    Thakur, Pallavi
    Kumaraswamy, Boyapelly
    Reddy, Gurram Raji
    Bandichhor, Rakeshwar
    Mukkantii, Khagga
    TETRAHEDRON-ASYMMETRY, 2012, 23 (08) : 547 - 553
  • [40] STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-ZIZAENE
    COATES, RM
    SOWERBY, RL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (15) : 5386 - &
12345