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

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	44-68
Number of pages	25
Journal	Arkivoc
Volume	2019
Issue number	4
DOIs	https://doi.org/10.24820/ark.5550190.p010.874
Publication status	Published - 1 Jan 2019
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

Keywords

Asymmetric hydrogenation
Asymmetric transfer hydrogenation
Diastereoselectivity
Enantioselectivity
Marine macrolides

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10.24820/ark.5550190.p010.874

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title = "Progress toward the total synthesis of mirabalin isomers",

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

U2 - 10.24820/ark.5550190.p010.874

DO - 10.24820/ark.5550190.p010.874

M3 - Article

AN - SCOPUS:85064227336

SN - 1551-7004

VL - 2019

SP - 44

EP - 68

JO - Arkivoc

JF - Arkivoc

IS - 4

ER -

Progress toward the total synthesis of mirabalin isomers

Abstract

UN SDGs

Keywords

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