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An easy and stereoselective synthesis of N-Boc-dolaproine via the Baylis–Hillman reaction

✍ Scribed by Wanda P. Almeida; Fernando Coelho

Book ID: 104252836
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 145 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02765-x

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✦ Synopsis

In this communication we report a stereoselective total synthesis of N-Boc-dolaproine (Dap), an amino acid residue of the antineoplastic pentapeptide Dolastatin 10. Our strategy is based on a Baylis-Hillman reaction between N-Boc-prolinal and methyl acrylate, followed by a diastereoselective double bond hydrogenation and hydrolysis of the ester function.

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