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
  • [1] Stereoselective Total Synthesis of (±)-Pleurospiroketals A and B
    Thorat, Sagar S.
    Krishna, Gamidi Rama
    Kontham, Ravindar
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (19): : 13572 - 13582
  • [2] The Stereoselective Total Synthesis of (+)-Stagonolide B
    Srihari, Pabbaraja
    Kumaraswamy, Boyapelly
    Somaiah, Ragam
    Yadav, Jhillu S.
    SYNTHESIS-STUTTGART, 2010, (06): : 1039 - 1045
  • [3] Stereoselective Total Synthesis of Polyrhacitides A and B
    Yadav, J. S.
    Rajendar, Goreti
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (33) : 6781 - 6788
  • [4] Stereoselective Total Synthesis of Attenols A and B
    Yadav, Jhillu S.
    Reddy, Poli Adi Narayana
    Reddy, Yerabolu Jayasudhan
    Meraj, Syeda
    Prasad, Attaluri R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (28) : 6317 - 6324
  • [5] Stereoselective Total Synthesis of (+)-Sapinofuranone B
    Yadav, J. S.
    Reddy, J. Shyam Sunder
    Mandal, S. S.
    Srihari, P.
    SYNLETT, 2010, (17) : 2636 - 2638
  • [6] Stereoselective total synthesis of Ieodomycin A and B
    Reddy, Emmadi Narender
    Krishnaiah, Atmakur
    Rao, Tadikamalla Prabhakar
    TETRAHEDRON-ASYMMETRY, 2013, 24 (12) : 724 - 728
  • [7] Stereoselective total synthesis of (+)-sapinofuranone B
    Yadav, J. S.
    Mandal, S. S.
    Reddy, J. S. S.
    Srihari, P.
    TETRAHEDRON, 2011, 67 (25) : 4620 - 4627
  • [8] Stereoselective Total Synthesis of (-)-Batzellasides A, B, and C
    Okaki, Toru
    Fujimura, Ryohei
    Sekiguchi, Masataka
    Zhou, Dejun
    Sugimoto, Kenji
    Minato, Daishiro
    Matsuya, Yuji
    Kato, Atsushi
    Adachi, Isao
    Tezuka, Yasuhiro
    Saporito, Ralph A.
    Toyooka, Naoki
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (14) : 2841 - 2848
  • [9] STEREOSELECTIVE TOTAL SYNTHESIS (+/-)-TRIMETHYLSEQUIRIN-B
    DAVIES, RV
    HATAM, NAR
    WHITING, DA
    JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (16): : 922 - &
  • [10] First stereoselective total synthesis of decytospolides A and B
    Krishna, Palakodety Radha
    Nomula, Rajesh
    Ramana, D. Venkata
    TETRAHEDRON LETTERS, 2012, 53 (28) : 3612 - 3614
12345