Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

Autor: Pierre-Antoine Nocquet, Aurélie Macé, Frédéric Legros, Jacques Lebreton, Gilles Dujardin, Sylvain Collet, Arnaud Martel, Bertrand Carboni, François Carreaux

Publikováno v: Beilstein Journal of Organic Chemistry, Vol 14, Iss 1, Pp 2949-2955 (2018)

In this paper, a new access to several chiral 3-aminoglycals as potential precursors for glycosylated natural products is reported from a common starting material, (−)-methyl-L-lactate. The stereodivergent strategy is based on the implementation of

Externí odkaz: https://doaj.org/article/9896b24e345f48058322f68eba14ab87

Diastereoselective Synthesis of trans -2,3-Diaryl(heteroaryl)-3,6-dihydropyrans by an Allylboration/Ring-Closing-Metathesis Sequence

Autor: Didier Berthelot, Janine Cossy, Ian Stansfield, Pierre-Antoine Nocquet, Patrick René Angibaud, Andrei Corbu, Lieven Meerpoel

Publikováno v: European Journal of Organic Chemistry. 2017:3343-3354

trans-2,3-Diaryl(heteroaryl) dihydropyrans were synthesized by an allylboration/ring-closing metathesis sequence, using allylboranes formed in situ from the corresponding allylic alcohol. Aryl(heteroaryl) substituents were thus installed dia-stereose

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::a176f3fcef4580944d00baf29e5da01c
https://doi.org/10.1002/ejoc.201700448

Total Synthesis of (±)-Scopolamine: Challenges of the Tropane Ring

Autor: Pierre-Antoine Nocquet, Till Opatz

Publikováno v: European Journal of Organic Chemistry. 2016:1156-1164

Scopolamine was synthesized using 6,7-dehydrotropine as a key intermediate. Rhodium-catalyzed [4 + 3] cycloaddition chemistry and a modified Robinson–Schopf reaction were each independently evaluated for their utility in constructing the tropane co

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::8e5da1018a030463b53863584dcd53e8
https://doi.org/10.1002/ejoc.201501430

Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

Autor: Jacques Lebreton, Gilles Dujardin, Frédéric Legros, Bertrand Carboni, Arnaud Martel, François Carreaux, Sylvain Collet, Aurélie Macé, Pierre-Antoine Nocquet

Publikováno v: Beilstein Journal of Organic Chemistry
Beilstein Journal of Organic Chemistry, 2018, 14, pp.2949-2955. ⟨10.3762/bjoc.14.274⟩
Beilstein Journal of Organic Chemistry, Vol 14, Iss 1, Pp 2949-2955 (2018)
Beilstein Journal of Organic Chemistry, Beilstein-Institut, 2018, 14, pp.2949-2955. ⟨10.3762/bjoc.14.274⟩

International audience; In this paper, a new access to several chiral 3-aminoglycals as potential precursors for glycosylated natural products is reported from a common starting material, (-)-methyl-L-lactate. The stereodivergent strategy is based on

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b05853c4861ee77b6370a5d29cd99f6f
https://univ-rennes.hal.science/hal-01973903

ChemInform Abstract: Total Synthesis of (.+-.)-Scopolamine: Challenges of the Tropane Ring

Autor: Till Opatz, Pierre-Antoine Nocquet

Publikováno v: ChemInform. 47

Scopolamine was synthesized using 6,7-dehydrotropine as a key intermediate. Rhodium-catalyzed [4 + 3] cycloaddition chemistry and a modified Robinson–Schopf reaction were each independently evaluated for their utility in constructing the tropane co

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::2ebf57a1bf6d2efb2daf5df5b9b40890
https://doi.org/10.1002/chin.201627230