Investigating direct routes to an advanced intermediate for the synthesis of C-20 diterpene alkaloids

被引:17
作者
Williams, CM [1 ]
Mander, LN
Bernhardt, PV
Willis, AC
机构
[1] Univ Queensland, Sch Mol & Microbial Sci, St Lucia, Qld 4072, Australia
[2] Australian Natl Univ, Res Sch Chem, Canberra, ACT, Australia
关键词
diterpene alkaloids; silver (I); intramolecular Friedel-Crafts arylation; 3-azabicyclo[3.3.1]nonane;
D O I
10.1016/j.tet.2005.02.014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rapid access to the ABCE ring system of the C-20 diterpene alkaloids was achieved by silver (I) promoted intramolecular Friedel-Crafts arylation of a functional group specific 5-bromo-3-azabicyclo[3.3.1]nonane derivative. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3759 / 3769
页数:11
相关论文
共 53 条
[1]  
ARDISSON J, 1992, B SOC CHIM FR, V129, P387
[2]   Diterpenoid and steroidal alkaloids [J].
Atta-ur-Rahman ;
Choudhary, MI .
NATURAL PRODUCT REPORTS, 1999, 16 (05) :619-635
[3]   SYNTHESIS OF THE A/E/F TRICYCLIC SECTION OF THE NORDITERPENOID ALKALOID METHYLLYCACONITINE, A POTENT INHIBITOR OF NEUROTRANSMISSION [J].
BAILLIE, LC ;
BEARDER, JR ;
WHITING, DA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (21) :2487-2488
[4]   Selective cleavage of isopropyl aryl ethers by aluminum trichloride [J].
Banwell, MG ;
Flynn, BL ;
Stewart, SG .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :9139-9144
[5]   Synthesis of ABE tricyclic analogues of methyllycaconitine using a Wacker oxidation-aldol strategy to append the B ring to the AE fragment [J].
Barker, D ;
Brimble, MA ;
McLeod, M ;
Savage, GP ;
Wong, DJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (07) :924-931
[6]   Application of olefin metathesis to the synthesis of ABE ring analogues of methyllycaconitine [J].
Barker, D ;
McLeod, MD ;
Brimble, MA ;
Savage, GP .
TETRAHEDRON LETTERS, 2002, 43 (34) :6019-6022
[7]   Hetisane-type diterpenoid alkaloids [J].
Bessonova, IA ;
Saidkhodzhaeva, SA .
CHEMISTRY OF NATURAL COMPOUNDS, 2000, 36 (05) :419-477
[8]   USE OF 2,6-DISUBSTITUTED CYCLOHEXANONES AND OF TROPINONE IN THE MANNICH REACTION [J].
BLICKE, FF ;
MCCARTY, FJ .
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (09) :1379-1380
[9]  
Bräse S, 1998, SYNTHESIS-STUTTGART, P148
[10]   STRUCTURE AND SYNTHESIS OF GOUDOTIANINE, A NEW 7-METHYLDEHYDROAPORPHINE FROM GUATTERIA-GOUDOTIANA [J].
CASTEDO, L ;
GRANJA, JA ;
DELERA, AR ;
VILLAVERDE, MC .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (05) :1561-1566