Tetrahedron letters

Stereospecific synthesis of erythrocinchona alkaloids from secologanin

RT Brown, D Curless

Index: Brown, Richard T.; Curless, Dale Tetrahedron Letters, 1986 ,  vol. 27,  # 49  p. 6005 - 6008

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Citation Number: 14

Abstract

... Printed in Great Britain Pergamon Journals Ltd. STEREOSPECIFIC SYNTHESIS OFERYTHRO CINCHONA ALKALOIDS FROM SECOLOGANIN Richard T. Brown* and Dale Curless Department of Chemistry, The University , Manchester Ml3 9PL, UK ... These were separated by chromatography - (silica; CH2C12/Et20/Et2NH 13:lO:Z) and shown to be identical with authentic samples of (t)-dihydrocinchonine (7_) and I-)-dihydrocinchonidine (S). Page 4. ...

 Related Synthetic Route
methyl (2S,3R,4S)-3-ethyl-4-((E)-3-(quinolin-4-yl)allyl)-2-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate Structure

109922-58-9

methyl (2S,3R,4...

~%

1-((3R,4S)-3-ethyl-4-((3-(quinolin-4-yl)oxiran-2-yl)methyl)piperidin-1-yl)-2,2,2-trifluoroethanone Structure

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1-((3R,4S)-3-et...

(4S,5R)-methyl 5-ethyl-4-((E)-3-(quinolin-4-yl)allyl)-1,4,5,6-tetrahydropyridine-3-carboxylate Structure

109922-59-0

(4S,5R)-methyl ...

~%

1-((3R,4S)-3-ethyl-4-((3-(quinolin-4-yl)oxiran-2-yl)methyl)piperidin-1-yl)-2,2,2-trifluoroethanone Structure

109922-61-4

1-((3R,4S)-3-et...

methyl (2S,3R,4S)-3-ethyl-4-((E)-3-(quinolin-4-yl)allyl)-2-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate Structure

109922-58-9

methyl (2S,3R,4...

~%

(4S,5R)-methyl 5-ethyl-4-((E)-3-(quinolin-4-yl)allyl)-1,4,5,6-tetrahydropyridine-3-carboxylate Structure

109922-59-0

(4S,5R)-methyl ...


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