Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS)-(−)-8-methyl-5-pentyloctahydroindolizine (8-epi-indolizidine 209B) and [(1S,4R,9aS)-(−)-4-pentyloctahydro-2H-quinolizin-1-yl]methanol

Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS)-(−)-8-methyl-5-pentyloctahydroindolizine (8-epi-indolizidine 209B) and [(1S,4R,9aS)-(−)-4-pentyloctahydro-2H-quinolizin-1-yl]methanol

Background<p>Prior work from these laboratories has centred on the development of enaminones as versatile intermediates for the synthesis of alkaloids and other nitrogen-containing heterocycles. In this paper we describe the enantioselective synthesis of indolizidine and quinolizidine analogue...

Full description

Bibliographic Details
Main Authors:	Joseph P. Michael, Claudia Accone, Charles B. de Koning, Christiaan W. van der Westhuyzen
Format:	Article
Language:	English
Published:	Beilstein-Institut 2008-01-01
Series:	Beilstein Journal of Organic Chemistry
Online Access:	https://doi.org/10.1186/1860-5397-4-5

Similar Items

(±)-(4aR,5R,8S,8aR)-8-(tert-Butyldimethylsilyloxy)-2,5,8a-trimethyl-4a,5,8,8a-tetrahydronaphthalene-1,4-dione
by: Fernanda G. Finelli, et al.
Published: (2013-03-01)

(4aR,8aR)-2,3-Diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline
by: Heng-Yun Ye, et al.
Published: (2008-02-01)

(4aS,5R,7R,8S,8aR)-8-(1,3-Dioxolan-2-yl)-7,8-dimethyl-5-(1-methylethenyl)perhydronaphthalen-2-one
by: Maxime A. Siegler, et al.
Published: (2008-01-01)

rac-(4aR,8aR)-2,3-Diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline
by: Fang Chen, et al.
Published: (2008-07-01)

(1R,4R,6S,7R)-5,5-Dibromo-1,4,8,8-tetramethyltricyclo[5.4.1.04,6]dodecan-12-one
by: Mohamed Zaki, et al.
Published: (2014-05-01)

Crystal structure of (1R,2S,4R,7R,8S,9R)-3,3-dichloro-8,9-epoxy-4,8,12,12-tetramethyltricyclo[5.5.0.02,4]dodecane
by: Ahmed Benzalim, et al.
Published: (2015-08-01)

(4aR*,8aS*)-2,3-Diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline
by: W. Chen, et al.
Published: (2012-07-01)

8,8-Diethyl-1,4,5,8-tetrahydronaphthalene-1,4,5-trione
by: Ramiro Araya-Maturana, et al.
Published: (2009-02-01)

Steviamine, a new class of indolizidine alkaloid [(1R,2S,3R,5R,8aR)-3-hydroxymethyl- 5-methyloctahydroindolizine-1,2- diol hydrobromide]
by: Thompson, A, et al.
Published: (2009)

Steviamine, a new class of indolizidine alkaloid [(1R,2S,3R,5R,8aR)-3-hydroxymethyl-5-methyloctahydroindolizine-1,2-diol hydrobromide]
by: Amber L. Thompson, et al.
Published: (2009-11-01)

(4R,6S,7S,8S,8aS)-6-Ethyl-7,8-dihydroxy-4-methyl-1,2,3,5,6,7,8,8a-octahydroindolizin-4-ium iodide
by: Viktor Vr&#225;bel, et al.
Published: (2011-12-01)

(1S*,3R*,5S*,7S*)-4,4,8,8-Tetrachloro-1-isopropyl-5-methyltricyclo[5.1.0.03,5]octane
by: Koblandy M. Turdybekov, et al.
Published: (2014-04-01)

Potassium (1R,4R,5S,8S)-4,5,8-trihydroxy-3-oxo-2,6-dioxabicyclo[3.3.0]octane-4-sulfonate dihydrate
by: David L. Hughes, et al.
Published: (2013-01-01)

A Simple Entry to the 5,8-Disubstituted Indolizidine Skeleton via Hetero Diels-Alder Reaction
by: Juan Francisco Rodríguez-Caro, et al.
Published: (2023-10-01)

8-O-Acetyl-8-epi-9-deoxygoniopypyrone
by: Hoong-Kun Fun, et al.
Published: (2012-04-01)

(1S,4S,5S,8R)-8-Nitrooxy-2,6-dioxabicyclo[3.3.0]octan-4-yl 3,4,5-triacetoxybenzoate
by: Yue Zhang, et al.
Published: (2009-11-01)

Crystal structure of (13S*,13aR*)-2,3-dimethoxy-13-hydroxy-13a-methyl- 8-oxo-5,6,13,13a-tetrahydro-8H-dibenzo[a,g]quinolizine, C20H21NO4
by: Liu L., et al.
Published: (2002-12-01)

Crystal structure of (13S*,13aR*)-2,3-dimethoxy-13-hydroxy-13a-methyl- 8-oxo-5,6,13,13a-tetrahydro-8H-dibenzo[a,g]quinolizine, C20H21NO4
by: Liu L., et al.
Published: (2002-12-01)

Asymmetric synthesis of (4R,5R)-cytoxazone and (4R,5S)-epi-cytoxazone.
by: Davies, S, et al.
Published: (2004)

Crystal structure of (c-4a,c-8a)-1,4,4a,5,8,8a-hexahydro- 1,4,10,10-tetramethyl-r-1 ,c-4:t-5,t-8- dimethanophthalazine, [C7H8] [C3N2(CH3)4]
by: Peters K., et al.
Published: (2000-02-01)

Crystal structure of 2(R),3(S),4(R),4a(R),4b(R),5(R),8a(S),9a(S)-2- acetoxymethyl-5-tri-methylsilyI-7-iodo-3,4,4a,4b,5,8,8a,9a-octahydro- 2H-pyrano[2,3-b]-benzofuran-3,4-diol diacetate, C21H31lO8Si
by: Herden U., et al.
Published: (1997-12-01)

Crystal structure of 2(R),3(S),4(R),4a(R),4b(R),5(R),8a(S),9a(S)-2- acetoxymethyl-5-tri-methylsilyI-7-iodo-3,4,4a,4b,5,8,8a,9a-octahydro- 2H-pyrano[2,3-b]-benzofuran-3,4-diol diacetate, C21H31lO8Si
by: Herden U., et al.
Published: (1997-12-01)

3-(4-Chlorophenyl)-1-[(2R,4aR,8aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl]prop-2-en-1-one
by: Mohamed Tebbaa, et al.
Published: (2011-06-01)

A Multi-Step Chromatographic Approach to Purify Radically Generated Ferulate Oligomers Reveals Naturally Occurring 5-5/8-8(Cyclic)-, 8-8(Noncyclic)/8-O-4-, and 5-5/8-8(Noncyclic)-Coupled Dehydrotriferulic Acids
by: Martin Waterstraat, et al.
Published: (2018-06-01)

(1R*,5S*)-8-(2-Fluoro-4-nitrophenyl)-8-azabicyclo[3.2.1]octan-3-one
by: Tao Yang, et al.
Published: (2011-12-01)

Steviamine, a new class of indolizidine alkaloid [(1R,2S,3R,5R,8aR)-3-hydroxy-meth-yl-5-methyl-octa-hydro-indolizine-1,2-diol hydro-bromide].
by: Thompson, A, et al.
Published: (2009)

3,6-DIDEOXY-3,6-IMINO-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE AS A DIVERGENT INTERMEDIATE FOR THE SYNTHESIS OF HYDROXYLATED PYRROLIDINES - SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO-L-GULITOL, 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL, 2S,3S,4R-3,4-DIHYDROXYPROLINE AND (1S,2R,8S,8AR)-1,2,8-TRIHYDROXYOCTAHYDROINDOLIZINE [8-EPI-SWAINSONINE] - X-RAY CRYSTAL-STRUCTURE OF (1S,2R,8S,8AR)-1,2,8-TRIHYDROXY-5-OXO-OCTAHYDROINDOLIZINE
by: Austin, G, et al.
Published: (1987)

Ethyl (4aR*,7S*,8S*,8aS*)-1-oxo-7-phenyl-3,4,4a,7,8,8a-hexahydro-1H-isochromene-8-carboxylate
by: Xiu Qing Jiang, et al.
Published: (2010-06-01)

1,4,5,8-Tetraisopropylanthracene
by: Chitoshi Kitamura, et al.
Published: (2010-09-01)

(7R,8R,8aS)-8-Hydroxy-7-phenylperhydroindolizin-3-one
by: &#317;ubom&#237;r &#352;vorc, et al.
Published: (2009-04-01)

(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl benzoate
by: Radouane Oubabi, et al.
Published: (2014-08-01)

8-(4-Chlorobenzylidene)-4-(4-chlorophenyl)-2-phenyl-5,6,7,8-tetrahydroquinoline
by: Fangfang Jian, et al.
Published: (2010-06-01)

THE STEREOSPECIFIC SYNTHESIS OF (-)-(8R) AND (-)-(8S)-METHYLCANADINE
by: Baird, P, et al.
Published: (1988)

Transformative Si8R8 Siliconoids
by: Naohiko Akasaka, et al.
Published: (2018-10-01)

2-{1-[(6R,S)-3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl]ethylidene}-N-methylhydrazinecarbothioamide
by: Ana Paula Lopes de Melo, et al.
Published: (2023-11-01)

(1R,2S,4S,4aS,8S,8aS)-4-Hydroxy-8,8a-dimethyl-10-oxo-2,3,4,7,8,8a-hexahydro-1H-4a,1-(epoxymethano)naphthalen-2-yl acetate
by: Ouassila Selaïmia-Ferdjani, et al.
Published: (2013-06-01)

N-[(1aR,5aR,8R,9aR)-1,1-Dichloro-1a,5,5,7-tetramethyl-1a,2,3,4,5,5a,8,9-octahydro-1H-benzo[a]cyclopropa[b][7]annulen-8-yl]acetamide
by: Ahmed Benharref, et al.
Published: (2017-04-01)

4,5-Di-<i>tert</i>-butyl-1,3,6,8-tetraphenyl-4,5,8a,8b-tetrahydro-as-indacene
by: Shakira I. Colon-Madera, et al.
Published: (2023-06-01)

Crystal structure of 8,8'-(5,5',6,6',7,7',8,8'-octahydrobitetrazolo[1,5-a][1',5'-a'])bipyridine,(C5H7N4)2
by: Peters K., et al.
Published: (1998-04-01)

2-Ruled Calibrated 4-folds in R^7 and R^8
by: Lotay, J
Published: (2004)