Rapid Two-Directional Synthesis of the F-J Fragment of the Gambieric Acids by Iterative Double Ring-Closing Metathesis

D‐glucal is the starting point for the efficient synthesis of the F–J fragment of the gambieric acids (see scheme). The H‐ring diol was subjected to double two‐directional alkynyl ether formation, carbocupration ring‐closing metathesis, and hydroboration. The tricyclic G–I diol was then converted in...

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Published in	Angewandte Chemie (International ed.) Vol. 44; no. 38; pp. 6157 - 6162
Main Authors	Clark, J. Stephen, Kimber, Marc C., Robertson, Jerod, McErlean, Christopher S. P., Wilson, Claire
Format	Journal Article
Language	English
Published	Weinheim WILEY-VCH Verlag 26.09.2005 WILEY‐VCH Verlag Wiley
Subjects	Animals Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Chemistry Chemistry, Multidisciplinary Ciguatoxins - chemical synthesis Ciguatoxins - chemistry cyclization Dinoflagellida - chemistry Ethers, Cyclic - chemical synthesis Ethers, Cyclic - chemistry metathesis Molecular Structure natural products Physical Sciences polyethers Science & Technology POLYETHER SYNTHESIS SUB-UNITS BIOLOGICAL-ACTIVITIES CIGUATOXIN CTX3C cyclization POTENT ANTIFUNGAL SUBSTANCES POLYCYCLIC ETHERS DINOFLAGELLATE GAMBIERDISCUS-TOXICUS BREVETOXIN-B natural products polyethers metathesis PRACTICAL TOTAL-SYNTHESIS CHAIN SYNTHESIS
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Abstract	D‐glucal is the starting point for the efficient synthesis of the F–J fragment of the gambieric acids (see scheme). The H‐ring diol was subjected to double two‐directional alkynyl ether formation, carbocupration ring‐closing metathesis, and hydroboration. The tricyclic G–I diol was then converted into the F–J fragment by a sequence that involves another double two‐directional ring‐closing metathesis reaction.
AbstractList	D‐glucal is the starting point for the efficient synthesis of the F–J fragment of the gambieric acids (see scheme). The H‐ring diol was subjected to double two‐directional alkynyl ether formation, carbocupration ring‐closing metathesis, and hydroboration. The tricyclic G–I diol was then converted into the F–J fragment by a sequence that involves another double two‐directional ring‐closing metathesis reaction.
Author	McErlean, Christopher S. P. Clark, J. Stephen Wilson, Claire Robertson, Jerod Kimber, Marc C.
Author_xml	– sequence: 1 givenname: J. Stephen surname: Clark fullname: Clark, J. Stephen email: j.s.clark@nottingham.ac.uk organization: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK, Fax: (+44) 115-951-3564 – sequence: 2 givenname: Marc C. surname: Kimber fullname: Kimber, Marc C. organization: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK, Fax: (+44) 115-951-3564 – sequence: 3 givenname: Jerod surname: Robertson fullname: Robertson, Jerod organization: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK, Fax: (+44) 115-951-3564 – sequence: 4 givenname: Christopher S. P. surname: McErlean fullname: McErlean, Christopher S. P. organization: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK, Fax: (+44) 115-951-3564 – sequence: 5 givenname: Claire surname: Wilson fullname: Wilson, Claire organization: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK, Fax: (+44) 115-951-3564
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/16134189$$D View this record in MEDLINE/PubMed
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Keywords	POLYETHER SYNTHESIS SUB-UNITS BIOLOGICAL-ACTIVITIES CIGUATOXIN CTX3C cyclization POTENT ANTIFUNGAL SUBSTANCES POLYCYCLIC ETHERS DINOFLAGELLATE GAMBIERDISCUS-TOXICUS BREVETOXIN-B natural products polyethers metathesis PRACTICAL TOTAL-SYNTHESIS CHAIN SYNTHESIS
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Snippet	D‐glucal is the starting point for the efficient synthesis of the F–J fragment of the gambieric acids (see scheme). The H‐ring diol was subjected to double...
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SubjectTerms	Animals Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Chemistry Chemistry, Multidisciplinary Ciguatoxins - chemical synthesis Ciguatoxins - chemistry cyclization Dinoflagellida - chemistry Ethers, Cyclic - chemical synthesis Ethers, Cyclic - chemistry metathesis Molecular Structure natural products Physical Sciences polyethers Science & Technology
Title	Rapid Two-Directional Synthesis of the F-J Fragment of the Gambieric Acids by Iterative Double Ring-Closing Metathesis
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