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- Publisher Website: 10.1016/j.tetlet.2008.01.084
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Article: Acid-promoted sequential cationic cyclizations for the synthesis of (±)-taiwaniaquinol B
Title | Acid-promoted sequential cationic cyclizations for the synthesis of (±)-taiwaniaquinol B |
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Authors | |
Issue Date | 2008 |
Publisher | Pergamon. 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? |
Abstract | A 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 Identifier | http://hdl.handle.net/10722/168276 |
ISSN | 2023 Impact Factor: 1.5 2023 SCImago Journal Rankings: 0.323 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
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dc.contributor.author | Li, S | en_US |
dc.contributor.author | Chiu, P | en_US |
dc.date.accessioned | 2012-10-08T03:16:57Z | - |
dc.date.available | 2012-10-08T03:16:57Z | - |
dc.date.issued | 2008 | en_US |
dc.identifier.citation | Tetrahedron Letters, 2008, v. 49 n. 11, p. 1741-1744 | en_US |
dc.identifier.issn | 0040-4039 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/168276 | - |
dc.description.abstract | A 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.language | eng | en_US |
dc.publisher | Pergamon. The Journal's web site is located at http://www.elsevier.com/locate/tetlet | en_US |
dc.relation.ispartof | Tetrahedron Letters | en_US |
dc.title | Acid-promoted sequential cationic cyclizations for the synthesis of (±)-taiwaniaquinol B | en_US |
dc.type | Article | en_US |
dc.identifier.email | Chiu, P:pchiu@hku.hk | en_US |
dc.identifier.authority | Chiu, P=rp00680 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1016/j.tetlet.2008.01.084 | en_US |
dc.identifier.scopus | eid_2-s2.0-39149137187 | en_US |
dc.identifier.hkuros | 145489 | - |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-39149137187&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 49 | en_US |
dc.identifier.issue | 11 | en_US |
dc.identifier.spage | 1741 | en_US |
dc.identifier.epage | 1744 | en_US |
dc.identifier.isi | WOS:000253785600005 | - |
dc.publisher.place | United Kingdom | en_US |
dc.identifier.scopusauthorid | Li, S=7409245628 | en_US |
dc.identifier.scopusauthorid | Chiu, P=11140148700 | en_US |
dc.identifier.issnl | 0040-4039 | - |