Cover Picture: Unique Remote Regiocontrol by an N‐Oxide Group in the Synthesis of Isocaulibugulones A, B, C, and D (ChemistrySelect 17/2023)

The cover picture shows a switch between two reaction mechanisms. An elongated resonance with the N‐oxide group and the vinylogous effect of the oxoammonium group allowed a regioselection switch during an oxidative amination reaction, permitting the preparation of isocaulibugulones A, B, C, and D in...

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Published inChemistrySelect (Weinheim) Vol. 8; no. 17
Main Authors Castro, Joaquim A. M., Serikava, Bruno K., Naciuk, Fabrício F., Ligiéro, Carolina B. P., Morgon, Nelson H., Miranda, Paulo C. M. L.
Format Journal Article
LanguageEnglish
Published 05.05.2023
Subjects
Alkaloids
Heterocycles
Quinones
Reaction mechanisms
Regioselectivity
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Summary:The cover picture shows a switch between two reaction mechanisms. An elongated resonance with the N‐oxide group and the vinylogous effect of the oxoammonium group allowed a regioselection switch during an oxidative amination reaction, permitting the preparation of isocaulibugulones A, B, C, and D in a straightforward approach. Isocaulibugulones A and D were synthesized in four steps and 11‐36% global yield. A further late‐stage halogenation step at isocaulibugulone A led to counterparts B and C with 83‐94% yield. More information can be found in the Research Article by Paulo C. M. L. Miranda et al. (DOI: 10.1002/slct.202300347).
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202300631