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Generation and fate of a novel homochiral mesoionic dipole: synthesis of C-nucleoside analogs

Generation and fate of a novel homochiral mesoionic dipole: synthesis of C-nucleoside analogs
Generation and fate of a novel homochiral mesoionic dipole: synthesis of C-nucleoside analogs
A mesoionic acyclic C-nucleoside 4, generated readily from delta-gluconolactone in a few synthetic steps, serves as the chiral core to construct a series of functionalized nucleosides bearing 2-aza-7-thiabicycle[2.2.1]heptane or 2-(1H)-pyridone moieties as the aglycon. The key step involves a [3+2] cycloaddition of 4 with several olefinic dipolarophiles followed by hydrogen sulfide elimination with mercury(II) acetate.
diastereoselective synthesis, cycloaddition chemistry, systems, dihydrothiophenes, thioisomunchnones, aldehydes
0957-4166
223-226
Arévalo, María J.
b558503a-c361-471a-bb6d-3e59efcb18f2
Avalos, Martín
55d2a59e-8c35-4028-b6c5-bfdd7ecda5a4
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Arévalo, María J.
b558503a-c361-471a-bb6d-3e59efcb18f2
Avalos, Martín
55d2a59e-8c35-4028-b6c5-bfdd7ecda5a4
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f

Arévalo, María J., Avalos, Martín, Babiano, Reyes, Cintas, Pedro, Hursthouse, Michael B., Jiménez, José L., Light, Mark E. and Palacios, Juan C. (2002) Generation and fate of a novel homochiral mesoionic dipole: synthesis of C-nucleoside analogs. Tetrahedron: Asymmetry, 13 (3), 223-226. (doi:10.1016/S0957-4166(02)00104-0).

Record type: Article

Abstract

A mesoionic acyclic C-nucleoside 4, generated readily from delta-gluconolactone in a few synthetic steps, serves as the chiral core to construct a series of functionalized nucleosides bearing 2-aza-7-thiabicycle[2.2.1]heptane or 2-(1H)-pyridone moieties as the aglycon. The key step involves a [3+2] cycloaddition of 4 with several olefinic dipolarophiles followed by hydrogen sulfide elimination with mercury(II) acetate.

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More information

Published date: 12 March 2002
Keywords: diastereoselective synthesis, cycloaddition chemistry, systems, dihydrothiophenes, thioisomunchnones, aldehydes

Identifiers

Local EPrints ID: 19658
URI: http://eprints.soton.ac.uk/id/eprint/19658
ISSN: 0957-4166
PURE UUID: 6df9d471-bdf7-4ac3-9d46-5e6d15153d71
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 15 Feb 2006
Last modified: 18 Feb 2021 16:52

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