Stereocontrol by quaternary centres: a stereoselective synthesis of (-)-luminacin D

Nathan Bartlett; Leona Gross; Florent Péron; Daniel J Asby; Matthew D Selby; Ali Tavassoli; Bruno Linclau

doi:10.1002/chem.201304776

Stereocontrol by quaternary centres: a stereoselective synthesis of (-)-luminacin D

Nathan Bartlett, Leona Gross, Florent Péron, Daniel J Asby, Matthew D Selby, Ali Tavassoli, Bruno Linclau

Bristol Medical School (THS)

Research output: Contribution to journal › Article (Academic Journal) › peer-review

8 Citations (Scopus)

Abstract

Very high diastereoselectivity can be achieved by 1,3-chelation-controlled allylation of aldehydes that possess a non-chelating α-ether substituent, even if the α-position is a quaternary centre and/or a spiro-epoxide. This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin D.

Original language	English
Pages (from-to)	3306-10
Number of pages	5
Journal	Chemistry - A European Journal
Volume	20
Issue number	12
DOIs	https://doi.org/10.1002/chem.201304776
Publication status	Published - 17 Mar 2014

Research Groups and Themes

Cerebrovascular and Dementia Research Group

Keywords

Aldehydes
Benzaldehydes
Catalysis
Chelating Agents
Epoxy Compounds
Ether
Spiro Compounds
Stereoisomerism

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title = "Stereocontrol by quaternary centres: a stereoselective synthesis of (-)-luminacin D",

abstract = "Very high diastereoselectivity can be achieved by 1,3-chelation-controlled allylation of aldehydes that possess a non-chelating α-ether substituent, even if the α-position is a quaternary centre and/or a spiro-epoxide. This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin D.",

keywords = "Aldehydes, Benzaldehydes, Catalysis, Chelating Agents, Epoxy Compounds, Ether, Spiro Compounds, Stereoisomerism",

author = "Nathan Bartlett and Leona Gross and Florent P{\'e}ron and Asby, \{Daniel J\} and Selby, \{Matthew D\} and Ali Tavassoli and Bruno Linclau",

note = "{\textcopyright} 2014 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

year = "2014",

month = mar,

day = "17",

doi = "10.1002/chem.201304776",

language = "English",

volume = "20",

pages = "3306--10",

journal = "Chemistry - A European Journal",

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publisher = "John Wiley and Sons Inc",

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TY - JOUR

T1 - Stereocontrol by quaternary centres

T2 - a stereoselective synthesis of (-)-luminacin D

AU - Bartlett, Nathan

AU - Gross, Leona

AU - Péron, Florent

AU - Asby, Daniel J

AU - Selby, Matthew D

AU - Tavassoli, Ali

AU - Linclau, Bruno

PY - 2014/3/17

Y1 - 2014/3/17

N2 - Very high diastereoselectivity can be achieved by 1,3-chelation-controlled allylation of aldehydes that possess a non-chelating α-ether substituent, even if the α-position is a quaternary centre and/or a spiro-epoxide. This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin D.

AB - Very high diastereoselectivity can be achieved by 1,3-chelation-controlled allylation of aldehydes that possess a non-chelating α-ether substituent, even if the α-position is a quaternary centre and/or a spiro-epoxide. This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin D.

KW - Aldehydes

KW - Benzaldehydes

KW - Catalysis

KW - Chelating Agents

KW - Epoxy Compounds

KW - Ether

KW - Spiro Compounds

KW - Stereoisomerism

U2 - 10.1002/chem.201304776

DO - 10.1002/chem.201304776

M3 - Article (Academic Journal)

C2 - 24519660

SN - 0947-6539

VL - 20

SP - 3306

EP - 3310

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 12

ER -

Stereocontrol by quaternary centres: a stereoselective synthesis of (-)-luminacin D

Abstract

Research Groups and Themes

Keywords

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