Synthetic Studies on Acochlearine: Construction of the A/B/C/E/F Ring System

被引:9
作者
Fujioka, Kosuke [1 ]
Miyamoto, Naoya [1 ]
Toya, Hiroki [1 ]
Okano, Kentaro [1 ]
Tokuyama, Hidetoshi [1 ]
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Aoba 6-3, Sendai, Miyagi 9808578, Japan
关键词
alkaloids; halogenation; lactams; domino reaction; Mannich reaction; C-H functionalization; ALPHA-PICOLINE-BORANE; DITERPENOID ALKALOIDS; TRANSANNULAR AZIRIDINATION; REDUCTIVE AMINATION; RACEMULSONINE; ALDEHYDES; EFFICIENT; KETONES; WATER; CORE;
D O I
10.1055/s-0035-1560384
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthetic studies on acochlearine are described. The pentacyclic A/B/C/E/F ring system of acochlearine was constructed from a bicyclic enone via chemoselective reductive amination, one-pot bromination-intramolecular Mannich reaction cascade, and 6-electrocyclization.
引用
收藏
页码:621 / 625
页数:5
相关论文
共 37 条
[1]   Synthesis of the A/E/F sections of conaconitine, napelline and related diterpenoid alkaloids of the aconitine group [J].
Baillie, LC ;
Batsanov, A ;
Bearder, JR ;
Whiting, DA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (20) :3471-3478
[2]   Highly stereoselective 6π electrocyclization of bridged bicyclic 1,3,5-trienes [J].
Benson, Chantel L. ;
West, F. G. .
ORGANIC LETTERS, 2007, 9 (13) :2545-2548
[3]   Construction of functionalized B/C/D ring system of C19-diterpenoid alkaloids via intramolecular Diels-Alder reaction followed by Wagner-Meerwein rearrangement [J].
Cheng, Hang ;
Xu, Liang ;
Chen, De-Lin ;
Chen, Qiao-Hong ;
Wang, Feng-Peng .
TETRAHEDRON, 2012, 68 (04) :1171-1176
[4]  
Cherney EC, 2014, J AM CHEM SOC, V136, P12592, DOI [10.1021/ja507321J, 10.1021/ja507321j]
[5]   EXPERIMENTS DIRECTED TOWARD TOTAL SYNTHESIS OF TERPENES .1. SYNTHESIS OF 1 BETA, 9-DIMETHYL-6,6-ETHYLENEDIOXY-CIS-DECALONE-2 [J].
CHURCH, RF ;
SHRIDHAR, DR ;
IRELAND, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (03) :707-&
[6]   C-H Amination in synthesis: An approach to the assembly of the B/C/D ring system of aconitine [J].
Conrad, Rosemary M. ;
Du Bois, J. .
ORGANIC LETTERS, 2007, 9 (26) :5465-5468
[7]  
GUTHRIE RW, 1966, TETRAHEDRON LETT, P4645
[8]   Gallium(III)-Catalyzed Cycloisomerization Approach to the Diterpenoid Alkaloids: Construction of the Core Structure for the Hetidines and Hetisines [J].
Hamlin, Amy M. ;
Cortez, Felipe de Jesus ;
Lapointe, David ;
Sarpong, Richmond .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (18) :4854-4857
[9]   Studies toward the total synthesis of nominine [J].
Hutt, Oliver E. ;
Mander, Lewis N. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (26) :10130-10140
[10]   STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-ATISINE VIA INTRAMOLECULAR DOUBLE MICHAEL REACTION [J].
IHARA, M ;
SUZUKI, M ;
FUKUMOTO, K ;
KAMETANI, T ;
KABUTO, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1963-1964