An Efficient Formal Synthesis of (−)-Balanol by Using Ruthenium-Catalyzed Asymmetric Hydrogenation

Phansavath, Phannarath; Paule, Sébastien Duprat de; Ratovelomanana‐Vidal, Virginie; Genêt, Jean‐Pierre

doi:10.1002/1099-0690(200012)2000:23<3903::aid-ejoc3903>3.0.co;2-q

Cited by 38 publications

(3 citation statements)

References 32 publications

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“…A ten‐step sequence led with high diastereo‐ and enantioselectivities to a key precursor of the natural product, featuring the functionalized hexahydroazepine core (Scheme 38). [107] …”

Section: Synthetic Applicationsmentioning

confidence: 99%

Asymmetric Hydrogenation: Design of Chiral Ligands and Transition Metal Complexes. Synthetic and Industrial Applications.

Genêt

Phansavath

Ratovelomanana‐Vidal

2021

Israel Journal of Chemistry

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This personal account focuses on the development of atropisomeric ligands and chiral transition metal complexes and their applications to the asymmetric hydrogenation of alkenes, ketones and heteroaromatics using Ru(II) and Ir(III) catalysts in‐house developed. Particularly, effective scaled‐up development syntheses of SYNPHOS and DIFLUORPHOS have been successfully achieved and their steric and electronic profiling established. Going further, we demonstrated the utility of such homogeneous catalytic process highlighted with examples of industrial applications and total syntheses of biorelevant targets. Asymmetric hydrogenation provides a powerful tool for performing precise stereocontrolled transformations on valuable complex molecules.

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“…A ten‐step sequence led with high diastereo‐ and enantioselectivities to a key precursor of the natural product, featuring the functionalized hexahydroazepine core (Scheme 38). [107] …”

Section: Synthetic Applicationsmentioning

confidence: 99%

Asymmetric Hydrogenation: Design of Chiral Ligands and Transition Metal Complexes. Synthetic and Industrial Applications.

Genêt

Phansavath

Ratovelomanana‐Vidal

2021

Israel Journal of Chemistry

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“…α-Amino-β-keto ester derivatives are one of the fundamental structural subunits in natural products such as miuraenamides [ 1 ], and important building blocks for the synthesis of a variety of heterocyclic compounds [ 2 ] and pharmaceutically active products [ 3 – 5 ]. In addition, they are valuable intermediates for chiral α-amino acids [ 6 – 7 ], including β-hydroxy-α-amino acids [ 8 – 14 ].…”

Section: Introductionmentioning

confidence: 99%

N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters

Uno¹,

Kobayashi²,

Takemoto³

2012

Beilstein J. Org. Chem.

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SummaryAn efficient catalytic synthesis of α-amino-β-keto esters has been newly developed. Cross-coupling of various aldehydes with α-imino ester, catalyzed by N-heterocyclic carbene, leads chemoselectively to α-amino-β-keto esters in moderate to good yields with high atom efficiency. The reaction mechanism is discussed, and it is proposed that the α-amino-β-keto esters are formed under thermodynamic control.

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“…Those challenging molecules and especially their syn-and anti-1,3-diol sequences constitute an excellent target for our ongoing program on the use of ruthenium-mediated asymmetric hydrogenation for the preparation of biologically relevant natural products. [3][4][5] Moreover, this would allow us to valorize the SYNPHOS ® ligand, a chiral atropisomeric diphosphine recently developed by our group. 6 Our retrosynthetic analysis is based on a logical disconnection of dolabelides into two fragments corresponding to C(1)-C (14) and C(15)-C(30) of the natural product (Scheme 2).…”

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confidence: 99%

First Stereoselective Synthesis of the C(1)-C(13) Fragment of Dolabelides Using Ruthenium-SYNPHOS^®-Catalyzed Asymmetric Hydrogenation Reactions

Roux¹,

Desroy²,

Phansavath³

et al. 2005

Synlett

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The first stereocontrolled synthesis of the C(1)-C(13) fragment of cytotoxic macrolides dolabelides is reported. The C(3), C(7), C(9) and C(11) hydroxyl-bearing stereocenters were installed using ruthenium-mediated asymmetric hydrogenation reactions of the adequate b-keto esters and b-hydroxy ketone.Dolabelides A and B were isolated in 1995 from Japanese sea hare Dolabella auricularia. Two other similar marine macrolides dolabelides C and D were isolated from the same source in 1997 (Scheme 1). 1,2 These macrolides exhibit cytotoxicity against HeLa-S 3 cells with IC 50 values of 6.3, 1.3, 1.9 and 1.5 mg/mL, respectively. The dolabelides contain a 22-or 24-membered ring, including eleven stereogenic centers. Eight of them are hydroxyl or acetyl functions. Those challenging molecules and especially their syn-and anti-1,3-diol sequences constitute an excellent target for our ongoing program on the use of ruthenium-mediated asymmetric hydrogenation for the preparation of biologically relevant natural products. [3][4][5] Moreover, this would allow us to valorize the SYNPHOS ® ligand, a chiral atropisomeric diphosphine recently developed by our group. 6

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An Efficient Formal Synthesis of (−)-Balanol by Using Ruthenium-Catalyzed Asymmetric Hydrogenation

Cited by 38 publications

References 32 publications

Asymmetric Hydrogenation: Design of Chiral Ligands and Transition Metal Complexes. Synthetic and Industrial Applications.

Asymmetric Hydrogenation: Design of Chiral Ligands and Transition Metal Complexes. Synthetic and Industrial Applications.

N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters

First Stereoselective Synthesis of the C(1)-C(13) Fragment of Dolabelides Using Ruthenium-SYNPHOS^®-Catalyzed Asymmetric Hydrogenation Reactions

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An Efficient Formal Synthesis of (−)-Balanol by Using Ruthenium-Catalyzed Asymmetric Hydrogenation

Cited by 38 publications

References 32 publications

Asymmetric Hydrogenation: Design of Chiral Ligands and Transition Metal Complexes. Synthetic and Industrial Applications.

Asymmetric Hydrogenation: Design of Chiral Ligands and Transition Metal Complexes. Synthetic and Industrial Applications.

N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters

First Stereoselective Synthesis of the C(1)-C(13) Fragment of Dolabelides Using Ruthenium-SYNPHOS®-Catalyzed Asymmetric Hydrogenation Reactions

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First Stereoselective Synthesis of the C(1)-C(13) Fragment of Dolabelides Using Ruthenium-SYNPHOS^®-Catalyzed Asymmetric Hydrogenation Reactions