Synthesis of graphislactones A–D through a palladium-mediated biaryl coupling reaction of phenyl benzoate derivatives

Transition metals in organic synthesis: Highlights for the year 2005

“…The palladium-catalyzed intramolecular variation ("aromatic-Heck") using aromatic rings in place of alkenes in couplings with organic and halides and triflates [392][393][394] was used to prepare benanomicin B [395], cavicularin and riccardin C [396], 5,6-dihydro-4H,8H-pyrido[3,2,1-de]phenanthridin-8-one [397], GABA agonist [219,220], lamellarin D and lamellarin analogs [223,240], allocolchicinoid [341], rhazinilam [398], givocarcin M [399], isoneocryptolepine [400], graphislactones A-D [401] and fused benzazepinones [402].…”

Synthesis of fluorescent dibenzopyranones by the Diels-Alder reaction of 4-styrylcoumarins and N-phenylmaleimide and in situ aromatization using DDQ

“…The dibenzopyranone unit is present in many natural products, [1][2][3][4][5] such as alternariol, graphislactones, autumnariol, autumnariniol, and altenuisol, and in many biologically active compounds. [6][7] Such lactones have been used as intermediates in the synthesis of several pharmaceutically interesting compounds including progesterone, androgen, glucocorticoid modulators, [8][9][10] and endothelial cell proliferation inhibitors.…”

Synthesis of Dibenzo[c,e]oxepin‐5(7H)‐ones from Benzyl Thioethers and Carboxylic Acids: Rhodium‐Catalyzed Double CH Activation Controlled by Different Directing Groups

“…[18] Dibenzooxepinones and their analogues can be found in natural products and bioactive molecules (Scheme 1c). [19] Antitumor activity, [19a] tyrosine kinase inhibition activity, [19b,d] cytotoxic activity, [19c,20] and antimicrotubule activity [21] have beeni nvestigated for some of these molecules.T raditionally, this dibenzo [c,e]oxepin-5(7H)-one structure was constructed by asequence of conventional cross-coupling and CÀObondforming cyclization. Fore xample,t he biphenyl structure was mainly constructed from organohalides and/or organometal-Scheme 1.…”