Asymmetric Synthesis of Piperidines and Octahydroindolizines

Stephen G. Davies; Deri G. Hughes; Paul D. Price; Paul M. Roberts; Angela J. Russell; Andrew D. Smith; James E. Thomson; Oliver M. H. Williams

doi:10.1055/s-0029-1219346

Asymmetric Synthesis of Piperidines and Octahydroindolizines

Stephen G. Davies, Deri G. Hughes, Paul D. Price, Paul M. Roberts, Angela J. Russell, Andrew D. Smith, James E. Thomson, Oliver M. H. Williams

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

Abstract

The conjugate addition of a homochiral lithium amide to a xi-hydroxy-alpha,beta-unsaturated ester, followed by a one-pot, ring-closure-N-debenzylation protocol has been used in the asymmetric syntheses of (S)-coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts) and the bicyclic core of stellettamide A.

Original language	English
Pages (from-to)	567-570
Number of pages	4
Journal	Synlett
Issue number	4
DOIs	https://doi.org/10.1055/s-0029-1219346
Publication status	Published - Mar 2010

Keywords

asymmetric synthesis
lithium amides
piperidines
coniine
delta-coniceine
JASPINE-B PACHASTRISSAMINE
AMIDE CONJUGATE ADDITION
D-LYXO-PHYTOSPHINGOSINE
BETA-AMINO ACIDS
ENANTIOSELECTIVE SYNTHESIS
PUMILIOTOXIN ALKALOIDS
DERIVATIVES
INDOLIZIDINE
ALKYLATION
EFFICIENT

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title = "Asymmetric Synthesis of Piperidines and Octahydroindolizines",

abstract = "The conjugate addition of a homochiral lithium amide to a xi-hydroxy-alpha,beta-unsaturated ester, followed by a one-pot, ring-closure-N-debenzylation protocol has been used in the asymmetric syntheses of (S)-coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts) and the bicyclic core of stellettamide A.",

keywords = "asymmetric synthesis, lithium amides, piperidines, coniine, delta-coniceine, JASPINE-B PACHASTRISSAMINE, AMIDE CONJUGATE ADDITION, D-LYXO-PHYTOSPHINGOSINE, BETA-AMINO ACIDS, ENANTIOSELECTIVE SYNTHESIS, PUMILIOTOXIN ALKALOIDS, DERIVATIVES, INDOLIZIDINE, ALKYLATION, EFFICIENT",

author = "Davies, {Stephen G.} and Hughes, {Deri G.} and Price, {Paul D.} and Roberts, {Paul M.} and Russell, {Angela J.} and Smith, {Andrew D.} and Thomson, {James E.} and Williams, {Oliver M. H.}",

year = "2010",

month = mar,

doi = "10.1055/s-0029-1219346",

language = "English",

pages = "567--570",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "4",

}

TY - JOUR

T1 - Asymmetric Synthesis of Piperidines and Octahydroindolizines

AU - Davies, Stephen G.

AU - Hughes, Deri G.

AU - Price, Paul D.

AU - Roberts, Paul M.

AU - Russell, Angela J.

AU - Smith, Andrew D.

AU - Thomson, James E.

AU - Williams, Oliver M. H.

PY - 2010/3

Y1 - 2010/3

N2 - The conjugate addition of a homochiral lithium amide to a xi-hydroxy-alpha,beta-unsaturated ester, followed by a one-pot, ring-closure-N-debenzylation protocol has been used in the asymmetric syntheses of (S)-coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts) and the bicyclic core of stellettamide A.

AB - The conjugate addition of a homochiral lithium amide to a xi-hydroxy-alpha,beta-unsaturated ester, followed by a one-pot, ring-closure-N-debenzylation protocol has been used in the asymmetric syntheses of (S)-coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts) and the bicyclic core of stellettamide A.

KW - asymmetric synthesis

KW - lithium amides

KW - piperidines

KW - coniine

KW - delta-coniceine

KW - JASPINE-B PACHASTRISSAMINE

KW - AMIDE CONJUGATE ADDITION

KW - D-LYXO-PHYTOSPHINGOSINE

KW - BETA-AMINO ACIDS

KW - ENANTIOSELECTIVE SYNTHESIS

KW - PUMILIOTOXIN ALKALOIDS

KW - DERIVATIVES

KW - INDOLIZIDINE

KW - ALKYLATION

KW - EFFICIENT

U2 - 10.1055/s-0029-1219346

DO - 10.1055/s-0029-1219346

M3 - Article

SN - 0936-5214

SP - 567

EP - 570

JO - Synlett

JF - Synlett

IS - 4

ER -

Asymmetric Synthesis of Piperidines and Octahydroindolizines

Abstract

Keywords

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