Download e-book for iPad: 178 Topics in Current Chemistry: Small Ring Compounds in by Armin de Meijere, A. Brandi, F.M. Cordero, A. Goti, T. Hirao

By Armin de Meijere, A. Brandi, F.M. Cordero, A. Goti, T. Hirao

ISBN-10: 3540604952

ISBN-13: 9783540604952

This paintings on small ring compounds in natural synthesis covers cycloadditions onto methylene- and alkylidenecyclopropane, and selective variations of small ring compounds in redox reactions.

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Extra info for 178 Topics in Current Chemistry: Small Ring Compounds in Organic Synthesis V

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The first example reported in the literature refers to the cycloaddition of N-(phenylaminooxoethylidene)aniline N-oxide (249) to 2,2-dimethylmethylenecyclopropane(250). The authors report about the formation of a single 5-spirocyclopropane fused regioisomer 251 (Scheme 41) [63]. The impulse to the study of these cycloadditions came from the discovery that 5-spirocyclopropane isoxazolidines (or isoxazolines) undergo a thermal rearrangement resulting in the production of selectively substituted tetrahydro(or dihydro) pyrid-4-ones (Scheme 42) 1-64].

The cis-diethyl substituted methylenecyclopropane 346a (Table 27, entry 11), gave quantitatively a 2:1 mixture of diastereomeric isoxazolines 357a with nitrile oxide 343, the major being that one deriving from the attack of the nitrile oxide from the side of the less bulky methyl groups [90]. The isoxazoline 355 (Table 27, entry 9) served as precursor for the total synthesis of the amphibian alkaloid ( _ )-Pumiliotoxin C 358 (Scheme 50) [89]. The question of regioselectivity of the cycloaddition with alkylidenecyclopropanes was also addressed, in analogy with nitrones, and afforded somewhat different results (Table 28) [91, 67b].

310 Scheme 45 Table 25. Cycloadditions of nitrones to biocyclopropylidenes 3 and 311 Entry BCPs Nitrone 3 1~+ Me"N'O255 1 /--k 2 3 Reaction conditions Benzene, 60 °C, 30 days O280 Me~. ) ! ~---Iq. ~ 18 days Me" Mel "O" ~/ 320a + ~r--l~ ~ / 91 Me- Me O %r"CO2Me 320b 45 A. Goti et al. (Table 23, entry 1) identified as two pairs of 5-spirocyclopropanepyrroloisoxazolidines 288a and 288b and 4-spirocyclopropanepyrrolo-isoxazolidines 289a and 289b. The more regioselective nitrone 257 gives only two diastereoisomers 294a, b in almost 1:1 ratio (Table 23, entry 4).

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178 Topics in Current Chemistry: Small Ring Compounds in Organic Synthesis V by Armin de Meijere, A. Brandi, F.M. Cordero, A. Goti, T. Hirao


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