An efficient synthesis of (1R,4S)-1-methyl-8-methoxy-3-(4-toluenesulfonyl)-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine.: A formal synthesis of (-)-aphanorphine

被引：25

作者：

Hu, HW ^{[1
]}

Zhai, HB ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

SYNLETT | 2003年 / 14期

关键词：

aphanorphine; benzazepine; Friedel-Crafts alkylation; marine alkaloid; synthesis;

D O I：

10.1055/s-2003-42102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a highly efficient synthesis of (1R,4S)- 1-methyl-8-methoxy-3-(4-toluenesulfonyl)-2,3,4,5-tetrahydro- 1,4-methano-3-benzazepine in six steps from 5. The present work constitutes a new formal synthesis of marine alkaloid (-)-aphanorphine.

引用

页码：2129 / 2130

页数：2

共 50 条

[1] Synthesis of 2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepine via oxidative cleavage and reductive amination strategies
Brooks, PR
Caron, S
Coe, JW
Ng, KK
Singer, RA
Vazquez, E
Vetelino, MG
Watson, HH
Whritenour, DC
Wirtz, MC
SYNTHESIS-STUTTGART, 2004, (11): : 1755 - 1758
[2] SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 2,3,4,5-TETRAHYDRO-1,5-METHANO-1H-3-BENZAZEPINES
MAZZOCCHI, PH
STAHLY, BC
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (04) : 455 - 457
[3] Syntheses of the opioid substructures 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine and 2,3,4,5-tetrahydro-1,5-methano-1H-2-benzazepine
Coe, Jotham W.
Brooks, Paige R.
Vetelino, Michael G.
Bashore, Crystal G.
Bianco, Krista
Flick, Andrew C.
TETRAHEDRON LETTERS, 2011, 52 (09) : 953 - 954
[4] Stereoselective Synthesis of Novel 2-Alkenyl-2,3,4,5-tetrahydro-1,4-epoxy-1-benzazepines and 2-Alkenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ols
Acosta Quintero, Lina Maria
Palma, Alirio
Nogueras, Manuel
Cobo, Justo
SYNTHESIS-STUTTGART, 2012, 44 (24): : 3765 - 3782
[5] Synthesis of 2-trifluoromethyl-2,3,4,5-tetrahydro-1H-3-benzazepine derivatives
Kawase, M
Niwa, M
Nozaki, M
Motohashi, N
HETEROCYCLES, 1998, 48 (03) : 555 - 560
[6] SYNTHESIS OF 1-ALKOXY-2,3,4,5-TETRAHYDRO-3(1H)-BENZAZEPINE
LIKFORMAN, J
GARDENT, J
COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1969, 268 (26): : 2340 - +
[7] Investigations of alternative routes for 2,3,4,5-tetrahydro-1,5-methano-1H-3-benzazepines
Singer, RA
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U131 - U132
[8] SYNTHESIS OF 2,3,4,5-TETRAHYDRO-1,2,4-TRIAZIN-3-ONES
LOZANOVA, K
SIMOV, D
KALCHEVA, V
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1987, (09): : 1277 - 1279
[9] Stereocontrolled Synthesis of (1R,3R,4S)- and (1S,3R,4S)-3,4-diaminocyclopentanols
Guan, YS
Green, MA
Bergstrom, DE
SYNLETT, 1999, (04) : 426 - 428
[10] Synthesis of 2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepines and 11-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indoles
Katritzky, AR
Jain, R
Akhmedova, R
Xu, YJ
ARKIVOC, 2003, : 4 - 13

← 1 2 3 4 5 →