CHIRAL SYNTHESIS OF 6,7-BENZOMORPHANS - SYNTHESIS OF (-)1(S),2(S),4(R),6(R)-1,2,3,4,5,6-HEXAHYDRO-2,6-METHANO-8-METHOXY-1,3,4,6-TETRAMETHYL-3-BENZAZOCINE THROUGH THE CHROMIUM HEXACARBONYL MEDIATED CYCLIZATION OF 1(S),1'(R)-1,2-DIHYDRO-7-METHOXY-1,4-DIMETHYL-1-(N-METHYL-N-TRIFLUOROACETAMIDO-1'-METHYLETHAN-2'-YL)NAPHTHALENE

被引：9

作者：

SAINSBURY, M ^{[1
]}

MAHON, MF ^{[1
]}

WILLIAMS, CS ^{[1
]}

NAYLOR, A ^{[1
]}

SCOPES, DIC ^{[1
]}

机构：

[1] GLAXO GRP RES LTD,DEPT MED CHEM,WARE SG12 0DJ,HERTS,ENGLAND

来源：

TETRAHEDRON | 1991年 / 47卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)86456-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)1(S),2(S),4(R),6(R)-1,2,3,4,5,6-Hexahydro- 2, 6-methano-8-methoxy- 1,3,4,6-tetramethyl-3-benzazocine has been synthesised in 86% enantiomeric excess from the alpha-(eta-6-chromium tricarbonyl) complex of 1(S),1'(R)-1,2-dihydro-7-methoxy-1,4-dimethyl-1-(N-methyl-N-trifluoroacetamido-1'-methylethan-2'-yl)naphthalene. A precursor of this compound is 2(R),4(S)-4-(3-methoxyphenyl)-2,4-dimethylcyclohexanone which was obtained through an Enders' type C-methylation reaction of 4-(3-methoxyphenyl)4-methylcyclohexanone using SAMP as the reagent.

引用

页码：4195 / 4210

页数：16

共 50 条

[31] Synthesis of 4-(R)-naphthalene-2-yloxy-1-(1-phenyl-(S)-ethyl)-pyrrolidin-3-(R)-ol and 4-(S)-naphthalen-2-yloxy-1-(1-phenyl-(S)-ethyl)-pyrrolidin-3-(S)-ol:: Versatile chiral intermediates for synthesis
Holsworth, DD
Stier, M
Wei, W
Edmunds, JJ
Li, TS
Maiti, SN
SYNTHETIC COMMUNICATIONS, 2004, 34 (23) : 4421 - 4430
[32] STUDIES ON SYNTHESES OF HETEROCYCLIC-COMPOUNDS .511. STUDIES ON SYNTHESES OF ANALGESICS .36. SYNTHESIS OF 1,2,3,4,5,6-HEXAHYDRO-2,6-METHANO-6-PHENYL-2-BENZAZOCINE
KAMETANI, T
AOYAMA, T
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1973, 10 (03) : 291 - 295
[33] Discovery of Novel 7-[(1R,5S)-1-Amino-5-fluoro-3-azabicyclo[3.3.0]octan-3-yl]-6-fluoro-1-(1R,2S)-2-fluorocyclopropane]-8-(methoxy or methyl)quinolones
Komoriya, Satoshi
Odagiri, Takashi
Inagaki, Hiroaki
Nagamochi, Masatoshi
Miyauchi, Rie
Yoshida, Ken-ichi
Kitamura, Takahiro
Takahashi, Hisashi
CHEMICAL & PHARMACEUTICAL BULLETIN, 2019, 67 (01) : 47 - 58
[34] (2S,3a′R,4′R,5′S,6′R)-4′,5′-isoprolidenedioxy-6′-(trityloxymethyl)-2′-oxotetrahydro-1H-spiro[pyrrolidine-2,3′-pyrrolo[1,2-b]isoxazole]-1-carbaldehyde
Yu, Chu-Yi
Fu, Ying
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O3172 - O3173
[35] Crystal structure analysis of 4-R-phenyl-2,6-dimethyl- 3,5-N-(dimethylcarbamoyl)-1,4-dihydropyridines [R=2-nitro (1), 4-methoxy (2) and 3,4-dichloro (3)]
Bidya, Sagar, M.
Ravikumar, K.
Sadanandam, Y. S.
Zeitschrift fuer Kristallographie, 213 (04):
[36] SYNTHESIS AND SPECTROSCOPIC CHARACTERIZATIONS OF BOTH 1-ETHYL-4,8-DIHYDRO-10-METHOXY-3-METHYL-8-R(1)-6-R(2)-DIPYRAZOLO[3,4-B/4',3'-F][1,5]DIAZOCIN-5(1H)-ONES AND 1-ETHYL-1,4,8,9-TETRAHYDRO-3,9-DIMETHYL-8-R(1)-6-R(2)-DIPYRAZOLO[3,4-B/4',3'-F][1,5]DIAZOCINE-5,10-DIONES OF PHARMACEUTICAL INTEREST
MIGLIARA, O
LAMARTINA, L
RAINIERI, R
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (05) : 1589 - 1593
[37] (1R*,3R*,4S*)-4-(tert-butyldiphenylsilyloxy)-6,7-dimethoxy-1-methyl-3-phenyl-1,2,3,4-tetrahydroisoquinoline
Pizarro, JL
Arriortua, MI
Tellitu, I
Badia, D
Dominguez, E
Ochando, L
Amigo, JM
Debaerdemaeker, T
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1997, 53 : 355 - 358
[38] Synthesis and Molecular Structure of N-{(1R,5S)-3-Methyl-8-Oxo-1,3,4,5,6,8-Hexahydro-2H-1,5-Methanopyrido[1,2-α] [1,5]Diazocin-9-yl}Acetamide
Suponitskii, K. Yu.
Koval'skaya, A. V.
Tsypysheva, I. P.
CHEMISTRY OF NATURAL COMPOUNDS, 2014, 50 (03) : 581 - 582
[39] Synthesis and Molecular Structure of N-{(1R,5S)-3-Methyl-8-Oxo-1,3,4,5,6,8-Hexahydro-2H-1,5-Methanopyrido[1,2-α] [1,5]Diazocin-9-yl}Acetamide
K. Yu. Suponitskii
A. V. Koval’skaya
I. P. Tsypysheva
Chemistry of Natural Compounds, 2014, 50 : 581 - 582
[40] (1S, 3 ' S, 3a ' R, 6 ' S)-6 '-(2-Chlorophenyl)-3 '-[(2R,3S)-1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-2-oxo-3 ',3 ' a, 4 ',6 '-etrahydro-2H, 2 ' H-spiro[acenaphthylene-1,1 '-pyrrolo[1,2-c][1,3]thiazole]-2 ',2 '-dicarbonitrile
Devi, Seenivasan Karthiga
Srinivasan, Thothadri
Rajesh, Raju
Raghunathan, Raghavachary
Velmurugan, Devadasan
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O750 - +

← 1 2 3 4 5 →