Total synthesis of dolastatin 10 through ruthenium-catalyzed asymmetric hydrogenations

A total synthesis of dolastatin 10, a potent inhibitor of microtubule assembly, which displayed remarkable antineoplastic activity, is reported. Our synthetic approach was based upon ruthenium-promoted asymmetric hydrogenation of β-keto esters derived from ( S)-Boc-proline and ( S)-Boc-isoleucine fo...

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Published inTetrahedron Vol. 63; no. 27; pp. 6115 - 6123
Main Authors Mordant, Céline, Reymond, Sébastien, Tone, Hitoshi, Lavergne, Damien, Touati, Ridha, Ben Hassine, Bechir, Ratovelomanana-Vidal, Virginie, Genet, Jean-Pierre
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.07.2007
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BETA-HYDROXY ESTERS
DIPHOSPHINE LIGAND
ALPHA-AMINO
BOC-DOLAPROINE
KETO-ESTERS
ANTINEOPLASTIC AGENTS
RU-SYNPHOS(R)
STEREOSPECIFIC SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
DYNAMIC KINETIC RESOLUTION
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Summary:A total synthesis of dolastatin 10, a potent inhibitor of microtubule assembly, which displayed remarkable antineoplastic activity, is reported. Our synthetic approach was based upon ruthenium-promoted asymmetric hydrogenation of β-keto esters derived from ( S)-Boc-proline and ( S)-Boc-isoleucine for the construction of the two key units: (2 R,3 R)-Boc-dolaproine (Dap) and (3 R)-Boc-dolaisoleucine (Dil). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.03.036