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Alkenes Curtius rearrangement

The retrosynthetic analysis is outlined in Scheme 22. The amide was introduced by the Curtius rearrangement, and the macrolide 117 was formed by Horner-Emmons macrocyclization at the C2-C3 bond. The C17-C18 bond was constructed by the ring-opening of epoxide 118. 119 was formed via the Kocienski-Julia olefination at the C8-C9 bond. The cis-2,6-disubstituted tetrahydropyran in 120 was constructed by the Petasis-Ferrier rearrangement. The C4-C5 (Z)-trisubstituted alkene in 121 was formed by carbomet-allation to an alkyne. [Pg.162]

Preservation of alkene geometry in the Curtius rearrangement was a key feature in De Brabander s remarkable application of Shioiri methodology in the total synthesis of palmerolide Conversion of carboxylic acid 89 to dienyl acyl azide 90 utilized DPP A, and Curtius rearrangement to the ( )-... [Pg.154]

See other pages where Alkenes Curtius rearrangement is mentioned: [Pg.97]    [Pg.477]    [Pg.477]    [Pg.87]    [Pg.746]    [Pg.184]    [Pg.273]    [Pg.120]    [Pg.149]    [Pg.494]    [Pg.620]    [Pg.92]    [Pg.139]    [Pg.342]    [Pg.172]    [Pg.1084]    [Pg.798]    [Pg.396]    [Pg.397]    [Pg.477]    [Pg.798]   


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Curtius

Curtius rearrangement

Rearrangements alkenes

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