New PDF release: Aristoteles, Politica BB

By v. Jowett

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Bachi has been active in the evaluation of several endoperoxides as potential antimalarial agents [146, 147]. The active compounds were prepared through a very elegant domino process involving molecular oxygen (Scheme 51). Thiyl radical addition onto diene 154 led to an adduct that was trapped by dioxygen to yield 155. 5-Exo-trig cyclization of the hydroperoxyl radical delivered bicyclic radical 156, which was reduced to hydroperoxide 157. Triphenylphosphine-mediated reduction of 157 yielded alcohol 158 (70% over two steps) as an essentially 1 : 1 mixture of epimers at the benzylic position.

Cationic termination could also be used, after suitable oxidation of the final radical (Scheme 75) [211]. Thus, ester 252 was treated with base and ethylchloroformate to give anion 253, which was oxidized to malonyl radical 254 by the ferrocenium ion. Cyclization/oxidation gave cation 256, which yielded 93% of malonate 257 by loss of the TMS group. This adduct was further elaborated upon and led to a cyclopentanoid monoterpene, dihydronepetalactone. Scheme 74 Ferrocenium-mediated radical-polar crossover: TEMPO-trapping 52 M.

In the case where alkyl radicals were obtained from alkyliodide precursors, the acylation reaction could be carried out with catalytic amounts of promoter, since the generated phosphonyl radical did promote the chain reaction by itself. Miyabe et al. developed a tandem addition/cyclization reaction featuring an unprecedented addition of alkoxycarbonyl-stabilized radicals on oxime ethers [117], and leading to the diastereoselective formation of β-amino-γ lactone derivatives [118, 119]. The reaction proceeds smoothly in the absence of toxic tin hydride and heavy metals via a route involving a triethylboranemediated iodine atom-transfer process (Scheme 37).

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Aristoteles, Politica BB by v. Jowett


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