Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/17253
Share/Export:
logo share SHARE logo core CORE BASE
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE
Title

Syntesis of Chiral Dispiroacetals from Carbohydrates

AuthorsDorta, Rosa L.; Martín, Ángeles CSIC ORCID ; Salazar, José A.; Suárez, Ernesto CSIC ORCID
Issue Date6-Mar-1998
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 63(7): 2251-2261 (1998)
AbstractThe syntheses of trioxadispiroacetals from carbohydrates are described. (5R,7S,13R)-13-Methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane (23) and (5S,7S,13R)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane (24) were prepared starting from d-galactose. The construction of the lateral tetrahydrofuran and tetrahydropyran rings was realized by homologation at C1 and C6 by appropriate tethers possessing a terminal primary alcohol. The cyclization of these alcohols at C1 and C5, respectively, was performed with (diacetoxyiodo)benzene and iodine in order to generate the alkoxy radicals which undergo an intramolecular hydrogen abstraction reaction. The diastereoisomers (5R,7S,13S)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane (37) and (5S,7S,13S)-13-methoxy-1,6,8-trioxadispiro[4.1.5.3]pentadecane (38) were prepared starting from tri-O-acetyl-d-glucal using a suitable methodology in which homologation and intramolecular hydrogen abstraction were again the key steps. We believe that this protocol could be easily extended to other tricyclic dispiroacetal ring systems.
Description11 pages, 7 schemes.-- Printed version published Apr 3, 1998.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo972023a
Publisher version (URL)http://dx.doi.org/10.1021/jo972023a
URIhttp://hdl.handle.net/10261/17253
DOI10.1021/jo972023a
ISSN0022-3263
Appears in Collections:(IPNA) Artículos

Show full item record
Review this work

SCOPUSTM   
Citations

46
checked on May 15, 2022

WEB OF SCIENCETM
Citations

44
checked on May 12, 2022

Page view(s)

379
checked on May 16, 2022

Google ScholarTM

Check

Altmetric

Dimensions


WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.