Progress toward the total synthesis of mirabalin isomers

Pierre Georges Echeverria; Amandine Pons; Sébastien Prévost; Charlène Férard; Johan Cornil; Amandine Guérinot; Janine Cossy; Phannarath Phansavath; Virginie Ratovelomanana-Vidal

doi:10.24820/ark.5550190.p010.874

Progress toward the total synthesis of mirabalin isomers

Pierre Georges Echeverria
, Amandine Pons
, Sébastien Prévost
, Charlène Férard
, Johan Cornil
, Amandine Guérinot
, Janine Cossy
, Phannarath Phansavath
, Virginie Ratovelomanana-Vidal

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

Résumé

Key fragments of the cytotoxic marine macrolide mirabalin have been synthesized, by using a flexible strategy based on asymmetric reductions to control the hydroxy- and carbamate-bearing stereocenters. In particular, ruthenium or rhodium-mediated asymmetric hydrogenation and transfer hydrogenation were used in combination with a dynamic kinetic resolution to control two contiguous stereocenters in a single step.

langue originale	Anglais
Pages (de - à)	44-68
Nombre de pages	25
journal	Arkivoc
Volume	2019
Numéro de publication	4
Les DOIs	https://doi.org/10.24820/ark.5550190.p010.874
état	Publié - 1 janv. 2019
Modification externe	Oui

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10.24820/ark.5550190.p010.874

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abstract = "Key fragments of the cytotoxic marine macrolide mirabalin have been synthesized, by using a flexible strategy based on asymmetric reductions to control the hydroxy- and carbamate-bearing stereocenters. In particular, ruthenium or rhodium-mediated asymmetric hydrogenation and transfer hydrogenation were used in combination with a dynamic kinetic resolution to control two contiguous stereocenters in a single step.",

keywords = "Asymmetric hydrogenation, Asymmetric transfer hydrogenation, Diastereoselectivity, Enantioselectivity, Marine macrolides",

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AU - Echeverria, Pierre Georges

AU - Pons, Amandine

AU - Prévost, Sébastien

AU - Férard, Charlène

AU - Cornil, Johan

AU - Guérinot, Amandine

AU - Cossy, Janine

AU - Phansavath, Phannarath

AU - Ratovelomanana-Vidal, Virginie

N1 - Publisher Copyright: ©ARKAT USA, Inc

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Key fragments of the cytotoxic marine macrolide mirabalin have been synthesized, by using a flexible strategy based on asymmetric reductions to control the hydroxy- and carbamate-bearing stereocenters. In particular, ruthenium or rhodium-mediated asymmetric hydrogenation and transfer hydrogenation were used in combination with a dynamic kinetic resolution to control two contiguous stereocenters in a single step.

AB - Key fragments of the cytotoxic marine macrolide mirabalin have been synthesized, by using a flexible strategy based on asymmetric reductions to control the hydroxy- and carbamate-bearing stereocenters. In particular, ruthenium or rhodium-mediated asymmetric hydrogenation and transfer hydrogenation were used in combination with a dynamic kinetic resolution to control two contiguous stereocenters in a single step.

KW - Asymmetric hydrogenation

KW - Asymmetric transfer hydrogenation

KW - Diastereoselectivity

KW - Enantioselectivity

KW - Marine macrolides

UR - https://www.scopus.com/pages/publications/85064227336

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M3 - Article

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SN - 1551-7004

VL - 2019

SP - 44

EP - 68

JO - Arkivoc

JF - Arkivoc

IS - 4

ER -

Progress toward the total synthesis of mirabalin isomers

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