2020
DOI: 10.1021/acs.joc.0c01605
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Total Synthesis of Cladosins B and C

Abstract: A convergent synthetic route to the fungal metabolites cladosins B and C has been developed, affording these natural products in 29% and 27% overall yield, respectively. The cladosins are rare examples of hybrid polyketides featuring a 3-enamine tetramic acid group derived from l-valine. Key steps in this modular six-step sequence include a DMAP-mediated O- to C-acyl rearrangement to unite the side chains with the tetramic acid core and subsequent amine incorporation using either ammonium acetate or HMDS.

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Cited by 3 publications
(1 citation statement)
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“…287 Known terrestrial flavone chrysin 796 was isolated from Chaetomium globosum as a new MNP. 288 Completed total syntheses of fungal metabolites included those of wickerol B, 289 (+)-penostatin A and (+)-penostatin C, 290 versicotides A–C, 291 cladosin B, 292 spirograterpene A, 293 nafuredin B, 294 chondristerins I and J, 295 aspergillusene B 296 and yicathins B and C. 297…”
Section: Marine Microorganisms and Phytoplanktonmentioning
confidence: 99%
“…287 Known terrestrial flavone chrysin 796 was isolated from Chaetomium globosum as a new MNP. 288 Completed total syntheses of fungal metabolites included those of wickerol B, 289 (+)-penostatin A and (+)-penostatin C, 290 versicotides A–C, 291 cladosin B, 292 spirograterpene A, 293 nafuredin B, 294 chondristerins I and J, 295 aspergillusene B 296 and yicathins B and C. 297…”
Section: Marine Microorganisms and Phytoplanktonmentioning
confidence: 99%