A Concise Approach to a Gelsemine Core Structure using an Oxygen to Carbon Bridge Swapping Strategy

K Tchabanenko; Nigel Simpkins; L Male

doi:10.1021/ol801835q

A Concise Approach to a Gelsemine Core Structure using an Oxygen to Carbon Bridge Swapping Strategy

K Tchabanenko, Nigel Simpkins, L Male

Chemistry

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13 Citations (Scopus)

Abstract

A tricyclic core structure 2 related to gelsemine 1 was synthesized from an oxabicyclo[3.2.1]octanone 4 by a three-step bridge swapping strategy involving elimination of the bridging ether oxygen and intramolecular Michael addition of a tethered cyanoacetamide unit.

Original language	English
Pages (from-to)	4747-4750
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	21
DOIs	https://doi.org/10.1021/ol801835q
Publication status	Published - 1 Nov 2008

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title = "A Concise Approach to a Gelsemine Core Structure using an Oxygen to Carbon Bridge Swapping Strategy",

abstract = "A tricyclic core structure 2 related to gelsemine 1 was synthesized from an oxabicyclo[3.2.1]octanone 4 by a three-step bridge swapping strategy involving elimination of the bridging ether oxygen and intramolecular Michael addition of a tethered cyanoacetamide unit.",

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AU - Male, L

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N2 - A tricyclic core structure 2 related to gelsemine 1 was synthesized from an oxabicyclo[3.2.1]octanone 4 by a three-step bridge swapping strategy involving elimination of the bridging ether oxygen and intramolecular Michael addition of a tethered cyanoacetamide unit.

AB - A tricyclic core structure 2 related to gelsemine 1 was synthesized from an oxabicyclo[3.2.1]octanone 4 by a three-step bridge swapping strategy involving elimination of the bridging ether oxygen and intramolecular Michael addition of a tethered cyanoacetamide unit.

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SP - 4747

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JO - Organic Letters

JF - Organic Letters

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A Concise Approach to a Gelsemine Core Structure using an Oxygen to Carbon Bridge Swapping Strategy

Abstract

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