| Total synthesis of bryostatins: the development of methodology for the atom-economic and stereoselective synthesis of the ring C subunit. | |
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MedLine Citation:
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PMID: 21793057 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Bryostatins, a family of structurally complicated macrolides, exhibit an exceptional range of biological activities. The limited availability and structural complexity of these molecules makes development of an efficient total synthesis particularly important. This article describes our initial efforts towards the total synthesis of bryostatins, in which chemoselective and atom-economical methods for the stereoselective assembly of the ring C subunit were developed. A Pd-catalyzed tandem alkyne-alkyne coupling/6-endo-dig cyclization sequence was explored and successfully pursued in the synthesis of a dihydropyran ring system. Elaboration of this methodology ultimately led to a concise synthesis of the ring C subunit of bryostatins. |
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Authors:
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Barry M Trost; Alison J Frontier; Oliver R Thiel; Hanbiao Yang; Guangbin Dong |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. Date: 2011-07-26 |
Journal Detail:
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Title: Chemistry (Weinheim an der Bergstrasse, Germany) Volume: 17 ISSN: 1521-3765 ISO Abbreviation: Chemistry Publication Date: 2011 Aug |
Date Detail:
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Created Date: 2011-08-12 Completed Date: 2011-11-21 Revised Date: 2013-04-01 |
Medline Journal Info:
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Nlm Unique ID: 9513783 Medline TA: Chemistry Country: Germany |
Other Details:
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Languages: eng Pagination: 9762-76 Citation Subset: IM |
Copyright Information:
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Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
Affiliation:
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Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Bryostatins
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chemical synthesis*,
chemistry Catalysis Cyclization Macrolides / chemical synthesis*, chemistry Molecular Structure Palladium / chemistry* Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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GM33049/GM/NIGMS NIH HHS; R01 GM033049/GM/NIGMS NIH HHS; R01 GM033049-24/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Bryostatins; 0/Macrolides; 7440-05-3/Palladium |
| Comments/Corrections | |
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