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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Published in:Angewandte Chemie International Edition Vol. 58; no. 39; pp. 13749 - 13752
Main Authors: Karns, Alexander S., Ellis, Bryan D., Roosen, Philipp C., Chahine, Zeinab, Le Roch, Karine G., Vanderwal, Christopher D.
Format: Journal Article
Language:English
Published: WEINHEIM Wiley 23.09.2019
Wiley Subscription Services, Inc
Edition:International ed. in English
Subjects:
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
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Abstract 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.
AbstractList 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 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 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 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.
The flagship member of the antiplasmodial isocyanoterpenes, 7,20-diisocyanoadociane (DICA), was synthesized from dehydrocryptone in 10 steps, and 13 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 antimalarial isocyanoterpene, diisocyanoadociane, was constructed in ten steps from simple starting materials.
Author Vanderwal, Christopher D.
Chahine, Zeinab
Le Roch, Karine G.
Karns, Alexander S.
Ellis, Bryan D.
Roosen, Philipp C.
AuthorAffiliation [b] Institute for Integrative Genome Biology, Center for Infectious Disease and Vector Research, 900 University Avenue, Department of Molecular, Cell, and Systems Biology, University of California, Riverside, Riverside, CA 92521, USA
[a] 1102 Natural Sciences II, Department of Chemistry, University of California, Irvine, CA, 92697-2025, USA
AuthorAffiliation_xml – name: [a] 1102 Natural Sciences II, Department of Chemistry, University of California, Irvine, CA, 92697-2025, USA
– name: [b] Institute for Integrative Genome Biology, Center for Infectious Disease and Vector Research, 900 University Avenue, Department of Molecular, Cell, and Systems Biology, University of California, Riverside, Riverside, CA 92521, USA
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CitedBy_id crossref_primary_10_3390_app14010281
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Issue 39
Keywords terpenoids
stereocontrol
Birch reduction
ANTIMALARIAL ACTIVITY
ALKYLATION REACTIONS
ORGANOMAGNESIUM
total synthesis
ISONITRILES
antiplasmodial
ORGANOALUMINUM ADDITION
Language English
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Snippet The flagship member of the antiplasmodial isocyanoterpenes, 7,20‐diisocyanoadociane (DICA), was synthesized from dehydrocryptone in 10 steps, and in 13 steps...
The flagship member of the antiplasmodial isocyanoterpenes, 7,20-diisocyanoadociane (DICA), was synthesized from dehydrocryptone in 10 steps, and in 13 steps...
The flagship member of the antiplasmodial isocyanoterpenes, 7,20-diisocyanoadociane (DICA), was synthesized from dehydrocryptone in 10 steps, and 13 from...
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SubjectTerms antiplasmodial
Antiprotozoal agents
Birch reduction
Chemistry
Chemistry, Multidisciplinary
Cyclohexanone
Methylation
Physical Sciences
Reengineering (product)
Science & Technology
stereocontrol
Stereoisomers
Synthesis
terpenoids
total synthesis
Title Concise Synthesis of the Antiplasmodial Isocyanoterpene 7,20‐Diisocyanoadociane
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https://pubmed.ncbi.nlm.nih.gov/PMC6759395
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