Clostrindolin is an antimycobacterial pyrone alkaloid from: Clostridium beijerinckii
Anaerobic bacteria represent an underexplored source of bioactive natural products with unusual structural features. Here we report the isolation and structure elucidation of an antimycobacterial natural product, clostroindolin, produced by Clostridium beijerinckii. Furthermore, we provide first insights into structure activity relationships, which might guide the development of novel antibiotics against mycobacteria.
Schieferdecker, Sebastian,Shabuer, Gulimila,Knuepfer, Uwe,Hertweck, Christian
supporting information
p. 6119 - 6121
(2019/07/03)
Synthesis of 4-dialkylamino-and 3-halo-6-methyl-4-methoxy-2-pyranones and their 5,6-dihydro derivatives
A new procedure has been developed for preparation of 4-dialkylamino-6-methyl-2-pyranones and their 5,6-dihydro analogs by reaction of cyclic amines with 4-chloro- and 4-methoxy-2-pyranones. Chlorine and bromine can be introduced into position 3 of the 2-pyranone and 5,6-dihydro-2-pyranone rings via reaction of 4-methoxy derivatives with N-halosuccinimides. In the presence of two equivalents of N-halosuccinimide 3-halo-4-methoxy-6-methyl-5,6-dihydro-2-pyranone is converted into 3-halo-4-methoxy-6-methyl-2-pyranone.
Lokot,Pashkovskii,Lakhvich
p. 1350 - 1354
(2007/10/03)
Brominated Derivatives of 4-Hydroxy- and 4-Methoxy-6-methyl-2H-pyran-2-ones
Twenty-five different brominated derivatives of 4-hydroxy-6-methyl-2-pyrone (triacetic acid lactone) and 3-acetyl-4-hydroxy-6-methyl-2-pyrone (dehydroacetic acid) have been prepared.Fifteen derivatives have not been previously described and the preparations of a few known products have been improved.Bromination at C-3, C-5, methyl group at C-6 and deacetylations at C-3 have been the types of reactions used.
March, P. de,Moreno-Manas, M.,Pi, R.,Ripoll, I.,Sanchez-Fernando, F.
p. 1537 - 1542
(2007/10/02)
Functionalization at C-5 and at the C-6 Methyl Group of 4-Methoxy-6-methyl-2-pyrone
A new entry to C-5 substituted 4-hydroxy-6-methyl-2-pyrones has been achieved.The best conditions to prepare the monobromo and the dibromo derivatives at C-3 and the C-6 methyl group of the title pyrone have been defined.The synthetic applicability of the phosphonium salts at CH3-C-6 of both 4-methoxy-6-methyl-2-pyrone, 5, and dehydroacetic acid, 2, has also been evaluated.
Bacardit, R.,Moreno-Manas, M.,Pleixats, R.
p. 157 - 160
(2007/10/02)
Pyrones. IX. Synthetic approaches to the fungal metabolite phacidin and its derivatives