File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

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

TitleAcid-promoted sequential cationic cyclizations for the synthesis of (±)-taiwaniaquinol B
Authors
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?
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
2015 Impact Factor: 2.347
2015 SCImago Journal Rankings: 0.782
ISI Accession Number ID
References

 

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

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats