A Total Synthesis of (±)-Ceratopicanol via Palladium Catalyzed Reductive Cyclization

被引：0

作者：

Kim, Rira ^{[1
]}

Lee, Sanghyeon ^{[1
]}

Lee, Jaeyeon ^{[1
]}

Lee, Hee-Yoon ^{[1
]}

机构：

[1] Korea Adv Inst Sci & Technol, Dept Chem, Daejeon 34141, South Korea

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 31期

关键词：

Triquinane; Cyclization; Free radicals; Pd catalysis; Total synthesis; ENANTIOSELECTIVE TOTAL-SYNTHESIS; REARRANGEMENT;

D O I：

10.1002/ejoc.202000769

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient total synthesis of ceratopicanol was achieved through successive Pd catalyzed reductive cycloaddition and cyclization reactions. The Pd mediated cyclization reaction to form a triquinane structure demonstrated that a small structural difference changed the reaction pathway either to form different structures or reduced non-cyclized product depending on the reaction conditions.

引用

页码：4931 / 4936

页数：6

共 50 条

[41] Chemoenzymatic total synthesis of rotigotine via IRED-catalyzed reductive amination
Tang, Dongyu
Ma, Yaqing
Bao, Jinping
Gao, Shushan
Man, Shuli
Cui, Chengsen
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (19) : 3843 - 3847
[42] A NEW SYNTHESIS OF GAMMA-BUTYROLACTONES VIA PALLADIUM(II)-CATALYZED CYCLIZATION OF TRIMETHYLSILYLALKYNES
COMPAIN, P
VATELE, JM
GORE, J
SYNLETT, 1994, (11) : 943 - 945
[43] SYNTHESIS OF 2-DEOXY-L-RIBOSE VIA PALLADIUM(II)-CATALYZED CYCLIZATION
Miyazawa, Masahiro
Akita, Erika
Onda, Kazusi
Narantsetseg, Magsarjav
Minabe, Haruna
Yokoyama, Hajime
Hirai, Yoshiro
HETEROCYCLES, 2014, 89 (02) : 399 - 412
[44] Stereoselective Synthesis of Benzo[a]quinolizidines via Aerobic DDQ-Catalyzed Allylation and Reductive Cyclization
Min, Sun-Joon
Jung, Sunhwa
Yoon, Seungri
Lee, Jae Kyun
ACS OMEGA, 2022, 7 (36): : 32562 - 32568
[45] One-Pot Palladium(II)-Catalyzed Synthesis of Fluorenones via Decarboxylative Cyclization
Cai, Zhiqiang
Hou, Xu
Hou, Ling
Hu, Zhiquan
Zhang, Bo
Jin, Zhengsheng
SYNLETT, 2016, 27 (03) : 395 - 398
[46] Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides
Iwata, Akira
Inuki, Shinsuke
Oishi, Shinya
Fujii, Nobutaka
Ohno, Hiroaki
TETRAHEDRON, 2015, 71 (37) : 6580 - 6585
[47] Versatile synthesis of 3-arylindan-1-ones by palladium-catalyzed intramolecular reductive cyclization of bromochalcones
Püschl, A
Rudbeck, HC
Faldt, A
Confante, A
Kehler, J
SYNTHESIS-STUTTGART, 2005, (02): : 291 - 295
[48] Palladium(II)-catalyzed cyclization of urethanes and its application to a total synthesis of 1-deoxynojirimycin
Yokoyama, Hajime
Kobayashi, Hisatake
Miyazawa, Masahiro
Yamaguchi, Seiji
Hirai, Yoshiro
HETEROCYCLES, 2007, 74 : 283 - 292
[49] Total Synthesis of (-)-Galanthamine and (-)-Lycoramine via Catalytic Asymmetric Hydrogenation and Intramolecular Reductive Heck Cyclization
Chen, Ji-Qiang
Xie, Jian-Hua
Bao, Deng-Hui
Liu, Sheng
Zhou, Qi-Lin
ORGANIC LETTERS, 2012, 14 (11) : 2714 - 2717
[50] Palladium-Catalyzed Copper-Free Sonogashira Coupling of 2-Bromoarylcarbonyls: Synthesis of Isobenzofurans via One-Pot Reductive Cyclization
Krishna Reddy, Alavala Gopi
Satyanarayana, Gedu
SYNTHESIS-STUTTGART, 2017, 49 (23): : 5149 - 5158

← 1 2 3 4 5 →