Synthesis of 6/7-Halotetralones

Synthesis and Antitumor Activity of Ring A- and F-Modified Hexacyclic Camptothecin Analogues

“…Compound 32 15 was oxidized with CrO 3 in AcOH at the peri-position of the acetamido group to give the desired tetralone, which afforded 33 by deprotection and hydrogenation. Bicyclic amino ketones 38, 43, 49, 50, 56, 61, and 65 for 5-substituted hexacyclic compounds were prepared from compounds 35, 16 40, 17 45, 16 53, 18 58, 19 and 63, 20 respectively, in several steps. (1) Phenylbutanoic acids were prepared as mentioned below.…”

Synthetic Studies toward Lapidilectine-Type Kopsia Alkaloids

“…1). 17 Despite the modest yield of this transformation, the usual ‘two-step’ Friedel-Crafts protocol, involving treatment of the corresponding acid chloride with a Lewis acid (e.g., AlCl 3 ) was less efficient and resulted in significant polymerization. Alternatively, aldehyde 23 was successfully converted to keto-tetracycle 25 (Eq.…”

Synthesis of Tricyclic Condensed Rings Incorporating the Pyrazole or Isoxazole Moieties Bonded to a 4-Piperidinyl Substituent

“…To begin the synthesis of the target derivatives E (Scheme 1), the known cyclic ketones 1a-c [6,7] were acylated by reaction of the corresponding sodium enolate, obtained by reaction with sodium hydride, with the reagent formed by reaction of the N-Boc protected isonipecotic acid 9 with 1,1′-carbonyldiimidazole [8] (Scheme 2). In this way, 1,3-dicarbonyl derivatives 2a-c were obtained in 62-63% yields.…”

“…The chloroketone 1a was a commercial compound. 6-Chloro-3,4-dihydronaphthalen-1-one (1b) [6], 7-chloro-2,3,4,5-tetrahydrobenzocyclo-heptan-1-one (1c) [7], N-Boc-nipecotic acid [8] and the piperidines 18 [10] and 19 [11] were obtained following the corresponding literature procedures.…”