Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry

William J. Kerr; Angus J. Morrison; Laura C. Paterson

doi:10.1016/j.tet.2015.06.003

Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry

William J. Kerr, Angus J. Morrison, Laura C. Paterson

Pure And Applied Chemistry

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Abstract

Biologically active α-methylenene propellanone has been synthesised in 12 steps in an overall yield of 11%. The key step of the synthesis, an intramolecular Pauson–Khand reaction, proceeds in good yield under alkyl sulfide promotion conditions, to furnish the 5,5-fused moiety within the target. Samarium diiodide-induced intramolecular conjugate addition onto the resulting cyclopentenone was used to complete the intriguing [3.3.3] propellanone skeleton.

Original language	English
Pages (from-to)	5356–5361
Number of pages	6
Journal	Tetrahedron
Volume	71
Issue number	33
Early online date	6 Jun 2015
DOIs	https://doi.org/10.1016/j.tet.2015.06.003
Publication status	Published - 19 Aug 2015

Keywords

cobalt
cyclisation
α-methylene cyclopentanone
Pauson-Khand
samarium

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10.1016/j.tet.2015.06.003

Kerr-etal-T2015-synthesis-of-a-methylene-propellanoneAccepted author manuscript, 597 KBLicence: CC BY-NC-ND 4.0

Cite this

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title = "Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry",

abstract = "Biologically active α-methylenene propellanone has been synthesised in 12 steps in an overall yield of 11%. The key step of the synthesis, an intramolecular Pauson–Khand reaction, proceeds in good yield under alkyl sulfide promotion conditions, to furnish the 5,5-fused moiety within the target. Samarium diiodide-induced intramolecular conjugate addition onto the resulting cyclopentenone was used to complete the intriguing [3.3.3] propellanone skeleton.",

keywords = "cobalt, cyclisation, α-methylene cyclopentanone, Pauson-Khand, samarium",

author = "Kerr, {William J.} and Morrison, {Angus J.} and Paterson, {Laura C.}",

year = "2015",

month = aug,

day = "19",

doi = "10.1016/j.tet.2015.06.003",

language = "English",

volume = "71",

pages = "5356–5361",

journal = "Tetrahedron",

issn = "0040-4020",

number = "33",

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TY - JOUR

T1 - Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry

AU - Kerr, William J.

AU - Morrison, Angus J.

AU - Paterson, Laura C.

PY - 2015/8/19

Y1 - 2015/8/19

N2 - Biologically active α-methylenene propellanone has been synthesised in 12 steps in an overall yield of 11%. The key step of the synthesis, an intramolecular Pauson–Khand reaction, proceeds in good yield under alkyl sulfide promotion conditions, to furnish the 5,5-fused moiety within the target. Samarium diiodide-induced intramolecular conjugate addition onto the resulting cyclopentenone was used to complete the intriguing [3.3.3] propellanone skeleton.

AB - Biologically active α-methylenene propellanone has been synthesised in 12 steps in an overall yield of 11%. The key step of the synthesis, an intramolecular Pauson–Khand reaction, proceeds in good yield under alkyl sulfide promotion conditions, to furnish the 5,5-fused moiety within the target. Samarium diiodide-induced intramolecular conjugate addition onto the resulting cyclopentenone was used to complete the intriguing [3.3.3] propellanone skeleton.

KW - cobalt

KW - cyclisation

KW - α-methylene cyclopentanone

KW - Pauson-Khand

KW - samarium

UR - http://www.sciencedirect.com/science/journal/aip/00404020

U2 - 10.1016/j.tet.2015.06.003

DO - 10.1016/j.tet.2015.06.003

M3 - Article

VL - 71

SP - 5356

EP - 5361

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 33

ER -

Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry

Abstract

Keywords

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Industrial Case Account 2009

Cite this

Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry

Abstract

Keywords

Access to Document

Other files and links

Projects

Industrial Case Account 2009

Cite this