Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers via ?3-allylpalladium intermediates

Mikko Passiniemi; Ari M.P. Koskinen

doi:10.1039/C0OB00643B

Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers via ?3-allylpalladium intermediates

Mikko Passiniemi, Ari M.P. Koskinen

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Abstract

A short route for the synthesis of Pachastrissamine (Jaspine B), an anhydrosphingosine derivative, and all three of its diastereomers is presented. The route consists of only 9 steps from the commercially available Garner’s aldehyde. The furan framework is formed via an h3-allylpalladium intermediate.

Original language	English
Pages (from-to)	1774-1783
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	6
DOIs	https://doi.org/10.1039/C0OB00643B
Publication status	Published - 2011
MoE publication type	A1 Journal article-refereed

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10.1039/C0OB00643B

Asymmetric synthesis of Pachastrissamine (Jaspine B)Accepted author manuscript, 203 KBLicence: Unspecified

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title = "Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers via ?3-allylpalladium intermediates",

abstract = "A short route for the synthesis of Pachastrissamine (Jaspine B), an anhydrosphingosine derivative, and all three of its diastereomers is presented. The route consists of only 9 steps from the commercially available Garner{\textquoteright}s aldehyde. The furan framework is formed via an h3-allylpalladium intermediate.",

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AU - Passiniemi, Mikko

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AB - A short route for the synthesis of Pachastrissamine (Jaspine B), an anhydrosphingosine derivative, and all three of its diastereomers is presented. The route consists of only 9 steps from the commercially available Garner’s aldehyde. The furan framework is formed via an h3-allylpalladium intermediate.

UR - http://dx.doi.org/10.1039/C0OB00643B

U2 - 10.1039/C0OB00643B

DO - 10.1039/C0OB00643B

M3 - Article

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 6

ER -

Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers via ?3-allylpalladium intermediates

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