Preparation of New Pyridoacridine Derivatives and Formal Synthesis of 11-Hydroxyascididemine

Marine natural products

“…543 The syntheses of ascididemin 808 and 11-hydroxyascididemin 804, which are metabolites of Didemnum and Leptoclinides species, respectively, 544,545 employ similar methodologies. 546, 547 As part of a structure-activity study, ascididemin 808 and a number of analogs were synthesized and evaluated in a wide range of assays. 548 The N-methylpyridinium alkaloid sulcatin 809 from a Mediterranean specimen of Microcosmus vulgaris showed interesting in vitro antiproliferative activity.…”

An efficient synthesis of isotope‐labeled PD0331179 and its labeled metabolite

“…Therefore, we proposed to synthesize a protected phenylpropyne that should not be so volatile and can be readily isolated and the protection group of which can be removed as needed later. In literatures, both bis(diisopropylamino)borane and trimethylsilyl (TMS) groups were utilized before as a protection group of an alkyne (Scheme ). The former can be removed under aqueous acidic condition, such as 3N HCl, whereas the later can be performed in DMF under a basic condition such as KF .…”

Pyridoacridines in the 21st Century

“…Later formation of the new pyridine ring in 76 was afforded in one pot and four steps by silyl group removal, incorporation of a diformyl protected amino group (cf. similar use of sodium diformylamide and discussion of mechanism in Scheme and Scheme ), oxidation and cyclization with concomitant amino group deprotection …”

“…Synthesis of 4-amino-6H-pyrido[2,3,4-kl]acridin-6-one 76. [41] Scheme 32 and Scheme 33), oxidation and cyclization with concomitant amino group deprotection. [41] An alternative route (Scheme 24) [42] to a tetracyclic quinoneimine system 78 also started with a palladium-catalysed coupling, to generate the 4-(2-aminophenyl)quinoline 77.…”