Journal article
Regioselective Spirostan E-Ring Opening for the Synthesis of Dihydropyran Steroidal Frameworks
Organic letters, Vol.18(8), pp.1772-1775
04/15/2016
DOI: 10.1021/acs.orglett.6b00492
PMID: 27010180
Abstract
The regioselective opening of the ring E in spirostan sapogenins provides new dihydropyran derivatives. This novel side chain is obtained after a Lewis acid mediated acetolysis followed by an alkaline workup. The reaction mechanism is analyzed via density functional theory computations, and both experimental and computational data support the formation of an oxacarbenium intermediate. The behavior of the title skeletons under acidic conditions is also investigated.
Details
- Title: Subtitle
- Regioselective Spirostan E-Ring Opening for the Synthesis of Dihydropyran Steroidal Frameworks
- Creators
- J Ciciolil Hilario-Martínez - Universidad Autónoma de YucatánReyna Zeferino-Díaz - Universidad Autónoma de YucatánMiguel A Muñoz-Hernández - Universidad Autónoma del Estado de MorelosMa Guadalupe Hernández-LinaresJosé Luis Cabellos - Universidad Autónoma de YucatánGabriel Merino - Universidad Autónoma de YucatánJesús Sandoval-RamírezZhendong Jin - University of IowaMaría A Fernández-Herrera - Universidad Autónoma de Yucatán
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.18(8), pp.1772-1775
- DOI
- 10.1021/acs.orglett.6b00492
- PMID
- 27010180
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Grant note
- DOI: 10.13039/501100003141, name: Consejo Nacional de Ciencia y Tecnología, award: INFRA-252665; name: Centro Universitario de Vinculación y Transferencia de Tecnología, Benemérita Universidad Autónoma de Puebla; DOI: 10.13039/501100015029, name: Vicerrectoría de Investigación y Estudios de Posgrado, Benemérita Universidad Autónoma de Puebla
- Language
- English
- Date published
- 04/15/2016
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984365902702771
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