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Article: An adventure in synthesis inspired by the pseudolaric acids
Title | An adventure in synthesis inspired by the pseudolaric acids |
---|---|
Authors | |
Keywords | Carbonyl Ylide Copper Hydride Cycloaddition Pseudolaric Acid Reductive Aldol Rhodium Carbene |
Issue Date | 2012 |
Citation | Strategies And Tactics In Organic Synthesis, 2012, v. 8, p. 55-78 How to Cite? |
Abstract | This account describes efforts that culminated in the first total synthesis of pseudolaric acid A, an antitumor and antiangiogenic natural product. A first retrosynthesis based on a reductive aldol reaction failed to generate the desired carboskeleton with the correct relative stereochemistry, although the copper hydride-induced reductive aldol cyclization developed for this key step turned out to be a useful synthetic methodology on its own. A second retrosynthesis based on the carbene cyclization cycloaddition cascade reaction as the key step was ultimately successful in constructing pseudolaric acid A, as well as other natural products. |
Description | Also book chapter: An Adventure in Synthesis Inspired by the Pseudolaric Acids. In M. Harmata (Eds.), Strategies and Tactics in Organic Synthesis, v. 8, p. 55-78. San Diego, USA: Academic Press, 2012 |
Persistent Identifier | http://hdl.handle.net/10722/168664 |
ISSN | |
References |
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Chiu, P | en_US |
dc.date.accessioned | 2012-10-08T03:24:09Z | - |
dc.date.available | 2012-10-08T03:24:09Z | - |
dc.date.issued | 2012 | en_US |
dc.identifier.citation | Strategies And Tactics In Organic Synthesis, 2012, v. 8, p. 55-78 | en_US |
dc.identifier.issn | 1874-6004 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/168664 | - |
dc.description | Also book chapter: An Adventure in Synthesis Inspired by the Pseudolaric Acids. In M. Harmata (Eds.), Strategies and Tactics in Organic Synthesis, v. 8, p. 55-78. San Diego, USA: Academic Press, 2012 | - |
dc.description.abstract | This account describes efforts that culminated in the first total synthesis of pseudolaric acid A, an antitumor and antiangiogenic natural product. A first retrosynthesis based on a reductive aldol reaction failed to generate the desired carboskeleton with the correct relative stereochemistry, although the copper hydride-induced reductive aldol cyclization developed for this key step turned out to be a useful synthetic methodology on its own. A second retrosynthesis based on the carbene cyclization cycloaddition cascade reaction as the key step was ultimately successful in constructing pseudolaric acid A, as well as other natural products. | - |
dc.language | eng | en_US |
dc.relation.ispartof | Strategies and Tactics in Organic Synthesis | en_US |
dc.subject | Carbonyl Ylide | en_US |
dc.subject | Copper Hydride | en_US |
dc.subject | Cycloaddition | en_US |
dc.subject | Pseudolaric Acid | en_US |
dc.subject | Reductive Aldol | en_US |
dc.subject | Rhodium Carbene | en_US |
dc.title | An adventure in synthesis inspired by the pseudolaric acids | 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/B978-0-12-386540-3.00003-4 | en_US |
dc.identifier.scopus | eid_2-s2.0-84864487719 | en_US |
dc.identifier.hkuros | 212655 | - |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-84864487719&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 8 | en_US |
dc.identifier.spage | 55 | en_US |
dc.identifier.epage | 78 | en_US |
dc.identifier.scopusauthorid | Chiu, P=11140148700 | en_US |
dc.identifier.issnl | 1874-4818 | - |