Synthetic Racemate and Enantiomers of Cytosporone E, a Metabolite of an Endophytic Fungus, Show Indistinguishably Weak Antimicrobial Activity

The Total Synthesis of (±)‐Fumimycin

“…We intended to introduce the fumaric acid side chain by amidation of an atrisubstituted amine, which derives from 3 through N-deprotection (Scheme 2). The 1-propenyl side chain at C1 could be installed by a palladium-catalyzed cross-coupling of aryl bromide 4 with 1propene boronic acid [10] or (trialkyl)-1-propenyl stannane [11] (left pathway). Alternatively, we planned a two-step se-quence involving a Claisen rearrangement and subsequent olefin isomerization, by using allyl ether 5 (right pathway).…”

“…We first pursued the synthetic pathway through the bromination/cross-coupling sequence (Scheme 3), starting from sesamol (10). We hoped to achieve selective bromination at C5 of one of the intermediate compounds of the sequence.…”

Synthesis of Biofunctional Molecules of Microbial Origin

“…Cytosporones D and E (144, Figure 5.29) were reported to show strong antimicrobial activity, while the others were biologically inactive. 36 Commercially available methyl 3,4,5-trihydroxybenzoate (A) was chosen as the starting material. In the case of cytosporone C ( Figure 5.29), its structure was solved by X-ray analysis.…”

Total Synthesis of Cytosporone B

“…1 Some of them display antibacterial activity. [1][2][3] Particularly, a recent excellent report by Wu et al 4 has revealed that Cytosporone B acted as an agonist for Nur77. Nuclear receptors play important roles in numerous biological processes such as cell proliferation, differentiation, apoptosis, metabolism and development.…”