Second-Generation Synthesis of Azadirachtin: A Concise Preparation of the Propargylic Mesylate Fragment

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
Hauptverfasser: Boyer, Alistair, Veitch, Gemma E, Beckmann, Edith, Ley, Steven V
Format: Artikel
Sprache:eng
Schlagworte:
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
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200805395