Derivatives of Methyl 5-Methyl-4-oxo-1,2,4,5,8,8a- hexahydrocyclopropa[c]-pyrrolo[3,2-e]indole-7- carboxylate:  A Case of Inverse Electronic Effects on the Reactivity of CC-1065 Derivatives

Oxidant and Transition-Metal-Free Photoinduced Direct Oxidative Annulation of 1-Aryl-2-(furan/thiophen-2-yl)butane-1,3-diones

“…In the presence of an oxidant such as O 2 , I 2 , I 2 /CuCl 2 , or TCNE, − the intermediate I is converted into phenanthrene 2 by the elimination of two hydrogen atoms. It is the most commonly used method for the synthesis of phenanthrene analogues and related heterocyclic compounds. − …”

Photocyclization of Tosylstilbenes as a Key Reaction in the Preparation of an Analogue of the Antitumor Agent CC-1065

“…Deprotection of the tosylated phenol and the alcohol in compound 17 by treatment with KOH led to benzoindoline 18 , which was subjected to an intramolecular Mitsunobu reaction with DEAD and triphenylphosphine, giving the acetylated compound 19 . The acetyl group in 19 could be removed under very mild conditions using sodium methoxide because the nitrogen atom in the resulting compound 7 belongs to a vinylogous amide.…”

Photochemistry of Tosylstilbenoids in the Preparation of Complex Heterocyclic Compounds. Synthesis of a Cyclopropafuroindolone Analogue of the DNA-Alkylating Section of the Antitumor Compound CC-1065

“…To find therapeutically useful compounds with maximum potency and minimum toxicity, a large collection of nonnatural derivatives was prepared . The central and right fragments interact in a noncovalent manner and increase the affinity for DNA, while the left fragment produces the alkylation of DNA by the attack of an adenine on the electrophilic cyclopropane ring.…”