Application of a Raney-cobalt-mediated tandem reductive cyclization protocol to total syntheses of the aspidosperma alkaloids (±)- limaspermidine and (±)-1-acetylaspidoalbidine

Shen H. Tan; Martin G. Banwell; Anthony C. Willis; Tristan A. Reekie

doi:10.1021/ol3026846

Application of a Raney-cobalt-mediated tandem reductive cyclization protocol to total syntheses of the aspidosperma alkaloids (±)- limaspermidine and (±)-1-acetylaspidoalbidine

Shen H. Tan, Martin G. Banwell^*, Anthony C. Willis, Tristan A. Reekie

^*Corresponding author for this work

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

58 Citations (Scopus)

Abstract

The racemic modification of the Aspidosperma alkaloid limaspermidine (1) has been prepared in ten steps including one involving a Raney-cobalt-mediated tandem reductive cyclization of nitrile 8 to give the tetracyclic system 9b. Compound (±)-1 has been converted over two steps into (±)-1-acetylaspidoalbidine [(±)-13].

Original language	English
Pages (from-to)	5621-5623
Number of pages	3
Journal	Organic Letters
Volume	14
Issue number	22
DOIs	https://doi.org/10.1021/ol3026846
Publication status	Published - 16 Nov 2012

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10.1021/ol3026846

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title = "Application of a Raney-cobalt-mediated tandem reductive cyclization protocol to total syntheses of the aspidosperma alkaloids (±)- limaspermidine and (±)-1-acetylaspidoalbidine",

abstract = "The racemic modification of the Aspidosperma alkaloid limaspermidine (1) has been prepared in ten steps including one involving a Raney-cobalt-mediated tandem reductive cyclization of nitrile 8 to give the tetracyclic system 9b. Compound (±)-1 has been converted over two steps into (±)-1-acetylaspidoalbidine [(±)-13].",

author = "Tan, {Shen H.} and Banwell, {Martin G.} and Willis, {Anthony C.} and Reekie, {Tristan A.}",

year = "2012",

month = nov,

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doi = "10.1021/ol3026846",

language = "English",

volume = "14",

pages = "5621--5623",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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Application of a Raney-cobalt-mediated tandem reductive cyclization protocol to total syntheses of the aspidosperma alkaloids (±)- limaspermidine and (±)-1-acetylaspidoalbidine. / Tan, Shen H.; Banwell, Martin G.; Willis, Anthony C. et al.
In: Organic Letters, Vol. 14, No. 22, 16.11.2012, p. 5621-5623.

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

TY - JOUR

T1 - Application of a Raney-cobalt-mediated tandem reductive cyclization protocol to total syntheses of the aspidosperma alkaloids (±)- limaspermidine and (±)-1-acetylaspidoalbidine

AU - Tan, Shen H.

AU - Banwell, Martin G.

AU - Willis, Anthony C.

AU - Reekie, Tristan A.

PY - 2012/11/16

Y1 - 2012/11/16

N2 - The racemic modification of the Aspidosperma alkaloid limaspermidine (1) has been prepared in ten steps including one involving a Raney-cobalt-mediated tandem reductive cyclization of nitrile 8 to give the tetracyclic system 9b. Compound (±)-1 has been converted over two steps into (±)-1-acetylaspidoalbidine [(±)-13].

AB - The racemic modification of the Aspidosperma alkaloid limaspermidine (1) has been prepared in ten steps including one involving a Raney-cobalt-mediated tandem reductive cyclization of nitrile 8 to give the tetracyclic system 9b. Compound (±)-1 has been converted over two steps into (±)-1-acetylaspidoalbidine [(±)-13].

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U2 - 10.1021/ol3026846

DO - 10.1021/ol3026846

M3 - Article

SN - 1523-7060

VL - 14

SP - 5621

EP - 5623

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Application of a Raney-cobalt-mediated tandem reductive cyclization protocol to total syntheses of the aspidosperma alkaloids (±)- limaspermidine and (±)-1-acetylaspidoalbidine

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