Stereocontrolled Synthesis of Adjacent Acyclic Quaternary-Tertiary Motifs: Application to a Concise Total Synthesis of (−)-Filiformin
Lithiation/borylation methodology has been developed for the synthesis of acyclic quaternary‐tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel‐type olefination enabled acyclic stereoco...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2014-05, Vol.53 (22), p.5552-5555 |
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| creator | Blair, Daniel J. Fletcher, Catherine J. Wheelhouse, Katherine M. P. Aggarwal, Varinder K. |
| description | Lithiation/borylation methodology has been developed for the synthesis of acyclic quaternary‐tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel‐type olefination enabled acyclic stereocontrol to be transformed into cyclic stereocontrol. These key steps have been applied to the shortest enantioselective synthesis of (−)‐filiformin to date (9 steps) with full stereocontrol.
True to (fili)form: Lithiation/borylation methodology has been developed for the synthesis of acyclic quaternary‐tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel‐type olefination enabled acyclic stereocontrol to be transformed into cyclic stereocontrol. These key steps were applied to the enantioselective synthesis of (−)‐filiformin. |
| doi_str_mv | 10.1002/anie.201400944 |
| format | Article |
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True to (fili)form: Lithiation/borylation methodology has been developed for the synthesis of acyclic quaternary‐tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel‐type olefination enabled acyclic stereocontrol to be transformed into cyclic stereocontrol. These key steps were applied to the enantioselective synthesis of (−)‐filiformin.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201400944</identifier><identifier>PMID: 24757079</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>boron ; Boronic Acids - chemistry ; Bromobenzenes - chemical synthesis ; Bromobenzenes - chemistry ; Carbamates - chemistry ; enantioselectivity ; Esters ; Isomers ; lithium ; Lithium - chemistry ; Methodology ; natural products ; Stereochemistry ; Stereoisomerism ; Synthesis ; total synthesis</subject><ispartof>Angewandte Chemie International Edition, 2014-05, Vol.53 (22), p.5552-5555</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5214-1cff740264074be894eeb0c6d66c05de1e52f0e1b3e82c40969e9d80587ed5003</citedby><cites>FETCH-LOGICAL-c5214-1cff740264074be894eeb0c6d66c05de1e52f0e1b3e82c40969e9d80587ed5003</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201400944$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201400944$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24757079$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Blair, Daniel J.</creatorcontrib><creatorcontrib>Fletcher, Catherine J.</creatorcontrib><creatorcontrib>Wheelhouse, Katherine M. P.</creatorcontrib><creatorcontrib>Aggarwal, Varinder K.</creatorcontrib><title>Stereocontrolled Synthesis of Adjacent Acyclic Quaternary-Tertiary Motifs: Application to a Concise Total Synthesis of (−)-Filiformin</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Lithiation/borylation methodology has been developed for the synthesis of acyclic quaternary‐tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel‐type olefination enabled acyclic stereocontrol to be transformed into cyclic stereocontrol. These key steps have been applied to the shortest enantioselective synthesis of (−)‐filiformin to date (9 steps) with full stereocontrol.
True to (fili)form: Lithiation/borylation methodology has been developed for the synthesis of acyclic quaternary‐tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel‐type olefination enabled acyclic stereocontrol to be transformed into cyclic stereocontrol. These key steps were applied to the enantioselective synthesis of (−)‐filiformin.</description><subject>boron</subject><subject>Boronic Acids - chemistry</subject><subject>Bromobenzenes - chemical synthesis</subject><subject>Bromobenzenes - chemistry</subject><subject>Carbamates - chemistry</subject><subject>enantioselectivity</subject><subject>Esters</subject><subject>Isomers</subject><subject>lithium</subject><subject>Lithium - chemistry</subject><subject>Methodology</subject><subject>natural products</subject><subject>Stereochemistry</subject><subject>Stereoisomerism</subject><subject>Synthesis</subject><subject>total synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUFv0zAYhiMEYmNw5YgscRmHlM-xHSfcQrWOSWMIrZSjlTpfhIsbd7Yj6C-AMz-RX4JLRwVcdvJ3eN5H8vtm2VMKEwpQvGwHg5MCKAeoOb-XHVNR0JxJye6nmzOWy0rQo-xRCKvEVxWUD7OjgkshQdbH2bfriB6ddkP0zlrsyPV2iJ8wmEBcT5pu1WocImn0VlujyfuxTYGh9dt8jj6adJC3Lpo-vCLNZpOQNho3kOhIS6Zu0CYgmbvY2n_Fpz-__3iRz4w1vfNrMzzOHvStDfjk9j3JPszO5tM3-eW784tpc5nr9C-eU933kkNRcpB8iVXNEZegy64sNYgOKYqiB6RLhlWhOdRljXVXgagkdgKAnWSne-_Gu5sRQ1RrEzRa2w7oxqCoBAqpHlrejYqirjgtC5HQ5_-hKzemluxvqioqxmBHTfaU9i4Ej73aeLNODSoKarem2q2pDmumwLNb7bhcY3fA_8yXgHoPfDEWt3foVHN1cfa3PN9nTYj49ZBt_WdVSiaF-nh1rsRiAa8X05ni7Bel97u7</recordid><startdate>20140526</startdate><enddate>20140526</enddate><creator>Blair, Daniel J.</creator><creator>Fletcher, Catherine J.</creator><creator>Wheelhouse, Katherine M. 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These key steps have been applied to the shortest enantioselective synthesis of (−)‐filiformin to date (9 steps) with full stereocontrol.
True to (fili)form: Lithiation/borylation methodology has been developed for the synthesis of acyclic quaternary‐tertiary motifs with full control of relative and absolute stereochemistry, thus leading to all four possible isomers of a stereodiad. A novel intramolecular Zweifel‐type olefination enabled acyclic stereocontrol to be transformed into cyclic stereocontrol. These key steps were applied to the enantioselective synthesis of (−)‐filiformin.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24757079</pmid><doi>10.1002/anie.201400944</doi><tpages>4</tpages><edition>International ed. in English</edition><oa>free_for_read</oa></addata></record> |
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| subjects | boron Boronic Acids - chemistry Bromobenzenes - chemical synthesis Bromobenzenes - chemistry Carbamates - chemistry enantioselectivity Esters Isomers lithium Lithium - chemistry Methodology natural products Stereochemistry Stereoisomerism Synthesis total synthesis |
| title | Stereocontrolled Synthesis of Adjacent Acyclic Quaternary-Tertiary Motifs: Application to a Concise Total Synthesis of (−)-Filiformin |
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