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Article: Acid-promoted sequential cationic cyclizations for the synthesis of (±)-taiwaniaquinol B

TitleAcid-promoted sequential cationic cyclizations for the synthesis of (±)-taiwaniaquinol B
Authors
Li, SChiu, P
Issue Date2008
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetlet
Citation
Tetrahedron Letters, 2008, v. 49 n. 11, p. 1741-1744 How to Cite?
DOI: http://dx.doi.org/10.1016/j.tetlet.2008.01.084
AbstractA formal total synthesis of (±)-taiwaniaquinol B starting from (E/Z)-citral has been accomplished by sequential cationic cyclizations promoted by acids. The cyclization to an α-cyclogeranyl ketone derivative is promoted by Lewis acid, whereas the use of Brønsted acid promotes an olefin isomerization leading to undesired cyclizations. The final ring formation to give the hydrofluorenone skeleton is promoted by Brønsted acid. Thus, the choice of the acid in each step critically determined the cationic reaction pathways and cyclization outcome. © 2008 Elsevier Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/168276
ISSN
0040-4039
2021 Impact Factor: 2.032
2020 SCImago Journal Rankings: 0.541
ISI Accession Number ID
WOS:000253785600005
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorLi, Sen_US
dc.contributor.authorChiu, Pen_US
dc.date.accessioned2012-10-08T03:16:57Z-
dc.date.available2012-10-08T03:16:57Z-
dc.date.issued2008en_US
dc.identifier.citationTetrahedron Letters, 2008, v. 49 n. 11, p. 1741-1744en_US
dc.identifier.issn0040-4039en_US
dc.identifier.urihttp://hdl.handle.net/10722/168276-
dc.description.abstractA formal total synthesis of (±)-taiwaniaquinol B starting from (E/Z)-citral has been accomplished by sequential cationic cyclizations promoted by acids. The cyclization to an α-cyclogeranyl ketone derivative is promoted by Lewis acid, whereas the use of Brønsted acid promotes an olefin isomerization leading to undesired cyclizations. The final ring formation to give the hydrofluorenone skeleton is promoted by Brønsted acid. Thus, the choice of the acid in each step critically determined the cationic reaction pathways and cyclization outcome. © 2008 Elsevier Ltd. All rights reserved.en_US
dc.languageengen_US
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetleten_US
dc.relation.ispartofTetrahedron Lettersen_US
dc.titleAcid-promoted sequential cationic cyclizations for the synthesis of (±)-taiwaniaquinol Ben_US
dc.typeArticleen_US
dc.identifier.emailChiu, P:pchiu@hku.hken_US
dc.identifier.authorityChiu, P=rp00680en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1016/j.tetlet.2008.01.084en_US
dc.identifier.scopuseid_2-s2.0-39149137187en_US
dc.identifier.hkuros145489-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-39149137187&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume49en_US
dc.identifier.issue11en_US
dc.identifier.spage1741en_US
dc.identifier.epage1744en_US
dc.identifier.isiWOS:000253785600005-
dc.publisher.placeUnited Kingdomen_US
dc.identifier.scopusauthoridLi, S=7409245628en_US
dc.identifier.scopusauthoridChiu, P=11140148700en_US
dc.identifier.issnl0040-4039-

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