Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition

Stephen G. Davies; Ai M. Fletcher; Paul M. Roberts; Andrew D. Smith

doi:10.1016/j.tet.2009.09.104

Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition

Stephen G. Davies, Ai M. Fletcher, Paul M. Roberts, Andrew D. Smith

Research output: Contribution to journal › Article › peer-review

Abstract

Conjugate addition of lithium (R)-N-allyl-N-(alpha-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(alpha-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant P-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the Sedum family, and the corresponding five-, seven- and eight-membered ring homologues. (C) 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	10192-10213
Number of pages	22
Journal	Tetrahedron
Volume	65
Issue number	49
DOIs	https://doi.org/10.1016/j.tet.2009.09.104
Publication status	Published - 5 Dec 2009

Keywords

Lithium amides
Asymmetric synthesis
Ring-closing metathesis
Sedum alkaloids
Sedamine
CORRESPONDING BETA,GAMMA-UNSATURATED ESTERS
SHORT ENANTIOSELECTIVE SYNTHESIS
RING CLOSING METATHESIS
STEREOSELECTIVE-SYNTHESIS
PIPERIDINE ALKALOIDS
(E)-ALPHA,BETA-UNSATURATED ESTERS
SUBSTITUTED PIPERIDINES
ABSOLUTE-CONFIGURATION
(S)-HOMOPIPECOLIC ACID
LOBELIA-INFLATA

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10.1016/j.tet.2009.09.104

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title = "Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition",

abstract = "Conjugate addition of lithium (R)-N-allyl-N-(alpha-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(alpha-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant P-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the Sedum family, and the corresponding five-, seven- and eight-membered ring homologues. (C) 2009 Elsevier Ltd. All rights reserved.",

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author = "Davies, {Stephen G.} and Fletcher, {Ai M.} and Roberts, {Paul M.} and Smith, {Andrew D.}",

year = "2009",

month = dec,

day = "5",

doi = "10.1016/j.tet.2009.09.104",

language = "English",

volume = "65",

pages = "10192--10213",

journal = "Tetrahedron",

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publisher = "Elsevier",

number = "49",

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TY - JOUR

T1 - Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition

AU - Davies, Stephen G.

AU - Fletcher, Ai M.

AU - Roberts, Paul M.

AU - Smith, Andrew D.

PY - 2009/12/5

Y1 - 2009/12/5

N2 - Conjugate addition of lithium (R)-N-allyl-N-(alpha-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(alpha-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant P-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the Sedum family, and the corresponding five-, seven- and eight-membered ring homologues. (C) 2009 Elsevier Ltd. All rights reserved.

AB - Conjugate addition of lithium (R)-N-allyl-N-(alpha-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(alpha-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant P-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the Sedum family, and the corresponding five-, seven- and eight-membered ring homologues. (C) 2009 Elsevier Ltd. All rights reserved.

KW - Lithium amides

KW - Asymmetric synthesis

KW - Ring-closing metathesis

KW - Sedum alkaloids

KW - Sedamine

KW - CORRESPONDING BETA,GAMMA-UNSATURATED ESTERS

KW - SHORT ENANTIOSELECTIVE SYNTHESIS

KW - RING CLOSING METATHESIS

KW - STEREOSELECTIVE-SYNTHESIS

KW - PIPERIDINE ALKALOIDS

KW - (E)-ALPHA,BETA-UNSATURATED ESTERS

KW - SUBSTITUTED PIPERIDINES

KW - ABSOLUTE-CONFIGURATION

KW - (S)-HOMOPIPECOLIC ACID

KW - LOBELIA-INFLATA

U2 - 10.1016/j.tet.2009.09.104

DO - 10.1016/j.tet.2009.09.104

M3 - Article

SN - 0040-4020

VL - 65

SP - 10192

EP - 10213

JO - Tetrahedron

JF - Tetrahedron

IS - 49

ER -

Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition

Abstract

Keywords

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