Second-Generation Synthesis of Azadirachtin: A Concise Preparation of the Propargylic Mesylate Fragment
A second bite of the apple: A new and highly efficient synthesis of the propargylic mesylate fragment of azadirachtin has been accomplished (see scheme; Bn=benzyl, Ms=methanesulfonyl, PMB=para-methoxybenzyl, TBDPS=tert-butyldiphenylsilyl). An enantioselective catalytic hetero Diels-Alder reaction se...
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| Veröffentlicht in: | Angewandte Chemie (International ed.) 2009-02, Vol.48 (7), p.1317-1320 |
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| container_end_page | 1320 |
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| container_issue | 7 |
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| container_title | Angewandte Chemie (International ed.) |
| container_volume | 48 |
| creator | Boyer, Alistair Veitch, Gemma E Beckmann, Edith Ley, Steven V |
| description | A second bite of the apple: A new and highly efficient synthesis of the propargylic mesylate fragment of azadirachtin has been accomplished (see scheme; Bn=benzyl, Ms=methanesulfonyl, PMB=para-methoxybenzyl, TBDPS=tert-butyldiphenylsilyl). An enantioselective catalytic hetero Diels-Alder reaction sets up the stereocenter at C15, which then controls the installation of the remaining functionality in a total of only 17 steps. |
| doi_str_mv | 10.1002/anie.200805395 |
| format | Article |
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An enantioselective catalytic hetero Diels-Alder reaction sets up the stereocenter at C15, which then controls the installation of the remaining functionality in a total of only 17 steps.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.200805395</identifier><identifier>PMID: 19140148</identifier><language>eng</language><publisher>Weinheim: Wiley-VCH Verlag</publisher><subject>asymmetric catalysis ; Catalysis ; hetero Diels-Alder reaction ; Lactones - chemistry ; Limonins - chemical synthesis ; Limonins - chemistry ; Mesylates - chemical synthesis ; Mesylates - chemistry ; natural products ; Stereoisomerism ; total synthesis ; α-keto lactones</subject><ispartof>Angewandte Chemie (International ed.), 2009-02, Vol.48 (7), p.1317-1320</ispartof><rights>Copyright © 2009 WILEY‐VCH Verlag GmbH & Co. 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| ispartof | Angewandte Chemie (International ed.), 2009-02, Vol.48 (7), p.1317-1320 |
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| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | asymmetric catalysis Catalysis hetero Diels-Alder reaction Lactones - chemistry Limonins - chemical synthesis Limonins - chemistry Mesylates - chemical synthesis Mesylates - chemistry natural products Stereoisomerism total synthesis α-keto lactones |
| title | Second-Generation Synthesis of Azadirachtin: A Concise Preparation of the Propargylic Mesylate Fragment |
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