Estratégias sintéticas para o ácido nonático

Nonactic acid 1 has been synthesized in 12 steps from readily available (S)-(Ϫ)-ethyl lactate in 20% overall yield. The key ("NARC") sequence in this method involved anti-aldol addition of acylsultam 3 with aldehyde 4 followed by intramolecular oxymercuration. The efficiency and selectivity of the anti-aldol reaction was found to be critically dependent upon the ratio of Lewis acid to base. The intramolecular oxymercuration was also found to be highly diastereoselective and was attributed to allylic control consistent with previous studies in our group.

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rac-(Z)-Ethyl 2-bromo-2-[(3R,5R)-3-bromo-5-methyltetrahydrofuran-2-ylidene]acetate

Loiseau

Neier

Labat

et al. 2006

Acta Crystallogr C

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In the title compound, C9H12Br2O3, a (tetrahydrofuran-2-ylidene)acetate, the double bond has the Z form. In the tetrahydrofuran group, the relative configuration of the Br atom in the 3-position and the methyl group in the 5-position is anti. The compound crystallizes with two independent molecules per asymmetric unit and, in the crystal structure, the individual molecules are linked to their symmetry-equivalent molecules by C-H...O hydrogen bonds, so forming centrosymmetric hydrogen-bonded dimers.

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Estratégias sintéticas para o ácido nonático

Cited by 3 publications

References 8 publications

Resolution of methyl nonactate

Resolution of methyl nonactate

A nucleophilic addition ring closure [NARC]-based synthesis of (+) -nonactic acid

rac-(Z)-Ethyl 2-bromo-2-[(3R,5R)-3-bromo-5-methyltetrahydrofuran-2-ylidene]acetate

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