Enantioselective total syntheses of the alkaloids (-)-rhazinal, (-)-rhazinilam, (-)-leuconolam and (+)-epi-leuconolam

Martin G. Banwell; Daniel A.S. Beck; Anthony C. Willis

Enantioselective total syntheses of the alkaloids (-)-rhazinal, (-)-rhazinilam, (-)-leuconolam and (+)-epi-leuconolam

Martin G. Banwell^*, Daniel A.S. Beck, Anthony C. Willis

^*Corresponding author for this work

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

40 Citations (Scopus)

Abstract

The title alkaloids, (-)-1, (-)-2, (-)-4 and (+)-5 respectively, have each been prepared from the enantiomerically enriched (74% ee) tetrahydroindolizine 14 which is itself obtained via an organocatalyzed and enantioselective intramolecular Michael addition reaction of the pyrrole 13 incorporating an N-tethered and β,β-disubstituted acrylaldehyde moiety.

Original language	English
Pages (from-to)	163-174
Number of pages	12
Journal	Arkivoc
Volume	2006
Issue number	3
Publication status	Published - 10 Sept 2005

Cite this

@article{ff2e6da3ed16469bba04027dfdf45ad8,

title = "Enantioselective total syntheses of the alkaloids (-)-rhazinal, (-)-rhazinilam, (-)-leuconolam and (+)-epi-leuconolam",

abstract = "The title alkaloids, (-)-1, (-)-2, (-)-4 and (+)-5 respectively, have each been prepared from the enantiomerically enriched (74\% ee) tetrahydroindolizine 14 which is itself obtained via an organocatalyzed and enantioselective intramolecular Michael addition reaction of the pyrrole 13 incorporating an N-tethered and β,β-disubstituted acrylaldehyde moiety.",

keywords = "(+)-epi-leuconolam, (-)-leuconolam, (-)-rhazinal, (-)-rhazinilam, Enantioselective, Total synthesis",

author = "Banwell, \{Martin G.\} and Beck, \{Daniel A.S.\} and Willis, \{Anthony C.\}",

year = "2005",

month = sep,

day = "10",

language = "English",

volume = "2006",

pages = "163--174",

journal = "Arkivoc",

issn = "1551-7004",

publisher = "Arkat",

number = "3",

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TY - JOUR

T1 - Enantioselective total syntheses of the alkaloids (-)-rhazinal, (-)-rhazinilam, (-)-leuconolam and (+)-epi-leuconolam

AU - Banwell, Martin G.

AU - Beck, Daniel A.S.

AU - Willis, Anthony C.

PY - 2005/9/10

Y1 - 2005/9/10

N2 - The title alkaloids, (-)-1, (-)-2, (-)-4 and (+)-5 respectively, have each been prepared from the enantiomerically enriched (74% ee) tetrahydroindolizine 14 which is itself obtained via an organocatalyzed and enantioselective intramolecular Michael addition reaction of the pyrrole 13 incorporating an N-tethered and β,β-disubstituted acrylaldehyde moiety.

AB - The title alkaloids, (-)-1, (-)-2, (-)-4 and (+)-5 respectively, have each been prepared from the enantiomerically enriched (74% ee) tetrahydroindolizine 14 which is itself obtained via an organocatalyzed and enantioselective intramolecular Michael addition reaction of the pyrrole 13 incorporating an N-tethered and β,β-disubstituted acrylaldehyde moiety.

KW - (+)-epi-leuconolam

KW - (-)-leuconolam

KW - (-)-rhazinal

KW - (-)-rhazinilam

KW - Enantioselective

KW - Total synthesis

UR - https://www.scopus.com/pages/publications/27644502443

M3 - Article

SN - 1551-7004

VL - 2006

SP - 163

EP - 174

JO - Arkivoc

JF - Arkivoc

IS - 3

ER -

Enantioselective total syntheses of the alkaloids (-)-rhazinal, (-)-rhazinilam, (-)-leuconolam and (+)-epi-leuconolam

Abstract

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