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Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions

Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions
Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions
Short routes to enantiomerically pure indolizidine and quinolizidine alkaloids have been developed using imino-aldol reactions of enolates derived from phenyl 5-chlorovalerate. High levels of syn selectivity (dr 13–16:1) were obtained using lithium enolates of phenyl esters in combination with tert-butylsulfinyl imines. The imino-aldol adducts were deprotected and cyclized to afford (-)-epilupinine ((-)-2) and (-)-tashiromine ((-)-1) in two further steps.
1523-7060
3988-3991
Cutter, Amanda C.
695ec27a-ac9d-425a-b74b-65045e3a9927
Miller, Iain R.
03d5cf57-92b5-4615-be69-6e254218b192
Keily, John F.
2578e169-6bf6-46f7-9387-d2756b06b045
Bellingham, Richard K.
ffa421f3-f2fb-4de9-b3f1-bba3f18b8976
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Brown, Richard C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Cutter, Amanda C.
695ec27a-ac9d-425a-b74b-65045e3a9927
Miller, Iain R.
03d5cf57-92b5-4615-be69-6e254218b192
Keily, John F.
2578e169-6bf6-46f7-9387-d2756b06b045
Bellingham, Richard K.
ffa421f3-f2fb-4de9-b3f1-bba3f18b8976
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Brown, Richard C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5

Cutter, Amanda C., Miller, Iain R., Keily, John F., Bellingham, Richard K., Light, Mark E. and Brown, Richard C. D. (2011) Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions. Organic Letters, 13 (15), 3988-3991. (doi:10.1021/ol2015048).

Record type: Article

Abstract

Short routes to enantiomerically pure indolizidine and quinolizidine alkaloids have been developed using imino-aldol reactions of enolates derived from phenyl 5-chlorovalerate. High levels of syn selectivity (dr 13–16:1) were obtained using lithium enolates of phenyl esters in combination with tert-butylsulfinyl imines. The imino-aldol adducts were deprotected and cyclized to afford (-)-epilupinine ((-)-2) and (-)-tashiromine ((-)-1) in two further steps.

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More information

Published date: 11 July 2011
Organisations: Chemistry

Identifiers

Local EPrints ID: 336673
URI: http://eprints.soton.ac.uk/id/eprint/336673
ISSN: 1523-7060
PURE UUID: 44f8fdb8-f34a-4263-ae73-bf6157936d37
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Richard C. D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

Catalogue record

Date deposited: 02 Apr 2012 13:57
Last modified: 18 Feb 2021 16:52

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