Concise Synthesis of the Antiplasmodial Isocyanoterpene 7,20‐Diisocyanoadociane

The flagship member of the antiplasmodial isocyanoterpenes, 7,20‐diisocyanoadociane (DICA), was synthesized from dehydrocryptone in 10 steps, and in 13 steps from commercially available material. Our previous formal synthesis was reengineered, leveraging only productive transformations to deliver DI...

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Veröffentlicht in:	Angewandte Chemie International Edition Jg. 58; H. 39; S. 13749 - 13752
Hauptverfasser:	Karns, Alexander S., Ellis, Bryan D., Roosen, Philipp C., Chahine, Zeinab, Le Roch, Karine G., Vanderwal, Christopher D.
Format:	Journal Article
Sprache:	Englisch
Veröffentlicht:	WEINHEIM Wiley 23.09.2019 Wiley Subscription Services, Inc
Ausgabe:	International ed. in English
Schlagworte:	antiplasmodial Antiprotozoal agents Birch reduction Chemistry Chemistry, Multidisciplinary Cyclohexanone Methylation Physical Sciences Reengineering (product) Science & Technology stereocontrol Stereoisomers Synthesis terpenoids total synthesis terpenoids stereocontrol Birch reduction ANTIMALARIAL ACTIVITY ALKYLATION REACTIONS ORGANOMAGNESIUM total synthesis ISONITRILES antiplasmodial ORGANOALUMINUM ADDITION
ISSN:	1433-7851, 1521-3773, 1521-3773
Online-Zugang:	Volltext
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Zusammenfassung:	The flagship member of the antiplasmodial isocyanoterpenes, 7,20‐diisocyanoadociane (DICA), was synthesized from dehydrocryptone in 10 steps, and in 13 steps from commercially available material. Our previous formal synthesis was reengineered, leveraging only productive transformations to deliver DICA in fewer than half the number of steps of our original effort. Important contributions, in addition to the particularly concise strategy, include a solution to the problem of axial nucleophilic methylation of a late‐stage cyclohexanone, and the first selective synthesis and antiplasmodial evaluation of the DICA stereoisomer with both isonitriles equatorial. The flagship antiplasmodial isocyanoterpene, 7,20‐diisocyanoadociane (DICA), was constructed in ten steps from simple starting materials. An additional important contribution is a solution to the problem of axial nucleophilic methylation of a late‐stage cyclohexanone, and the first selective synthesis and antiplasmodial evaluation of the DICA stereoisomer with both isonitriles equatorial.
Bibliographie:	These authors contriuted equally to this work. NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 These authors contributed equally.
ISSN:	1433-7851 1521-3773 1521-3773
DOI:	10.1002/anie.201906834