Total synthesis of (±)-jamtine using a thionium/N-acyliminium ion cascade

被引：77

作者：

Padwa, A ^{[1
]}

Danca, MD ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 05期

关键词：

D O I：

10.1021/ol017193v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The first total synthesis of (+/-)-jamtine (4), a tetrahydroisoquinoline alkaloid reputed for its therapeutic properties, is described. The key step involves a tandem thionium/N-acyliminium ion cyclization from enamido sulfoxide 13. The cascade process takes place with high diastereoselectivity and in excellent yield.

引用

页码：715 / 717

页数：3

共 50 条

[21] Synthesis of substituted pyrrolidines by sequential radical cyclization and N-acyliminium ion reactions
Matos, MRPN
Afonso, CAM
McGarvey, T
Lee, P
Batey, RA
TETRAHEDRON LETTERS, 1999, 40 (52) : 9189 - 9193
[22] IODIDE-TERMINATED N-ACYLIMINIUM ION/ALKENE CYCLIZATIONS - STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF ALOPERINE
BROSIUS, AD
OVERMAN, LE
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 459 - ORGN
[23] Furan-terminated N-acyliminium ion initiated cyclizations in alkaloid synthesis
Tanis, SP
Deaton, MV
Dixon, LA
McMills, MC
Raggon, JW
Collins, MA
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20): : 6914 - 6928
[24] N,N-Acetals as N-acyliminium ion precursors:: Synthesis and absolute stereochemistry of epiquinamide
Wijdeven, Marloes A.
Wijtmans, Roel
van den Berg, Rutger J. F.
Noorduin, Wim
Schoemaker, Hans E.
Sonke, Theo
van Delft, Floris L.
Blaauw, Richard H.
Fitch, Richard W.
Spande, Thomas F.
Daly, John W.
Rutjes, Floris P. J. T.
ORGANIC LETTERS, 2008, 10 (18) : 4001 - 4003
[25] Synthesis of homoallylic amines via N-acyliminium ion reactions on solid support
Meester, WJN
Rutjes, FPJT
Hermkens, PHH
Hiemstra, H
TETRAHEDRON LETTERS, 1999, 40 (08) : 1601 - 1604
[26] An efficient synthesis of substituted isoxazolopyrroloisoquinolines via diastereoselective N-acyliminium ion cyclization
Ledovskaya, Maria S.
Molchanov, Alexander P.
Boitsov, Vitaly M.
Kostikov, Rafael R.
Stepakov, Alexander V.
TETRAHEDRON, 2015, 71 (13) : 1952 - 1958
[27] A novel synthesis of (di)-benzazocinones via an endocyclic N-acyliminium ion cyclisation
King, Frank D.
Aliev, Abil E.
Caddick, Stephen
Tocher, D. A.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (05) : 1547 - 1554
[28] A Kulinkovich entry into tertiary N-acyliminium ion chemistry
Ollero, L
Mentink, G
Rutjes, FPJT
Speckamp, WN
Hiemstra, H
ORGANIC LETTERS, 1999, 1 (09) : 1331 - 1334
[29] Total synthesis of (±)-6-deoxycastanospermine:: an application of the addition of organoboronates to N-acyliminium ions
Batey, RA
MacKay, DB
TETRAHEDRON LETTERS, 2000, 41 (51) : 9935 - 9938
[30] Studies toward the total synthesis of the oxindole alkaloid gelsedine: An efficient allene-terminated N-acyliminium ion cyclization
vanHenegouwen, WGB
Hiemstra, H
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25): : 8862 - 8867

← 1 2 3 4 5 →