Publications 1992-1993

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153.     Zhang, Q.; Mohan, R. M.; Cook, L.; Kazanis, S.; Peisach, D.; Foxman, B. M.; Snider, B. B. “Asymmetric Induction in Manganese(III)-Based Oxidative Free-Radical Cyclizations of Phenylmenthyl Acetoacetates and 2,5-Dimethylpyrrolidine Acetoacetamides” J. Org. Chem. 1993, 58, 7640-7651. http://dx.doi.org/10.1021/jo00079a006

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152.     Snider, B. B.; Vo, N. H.; Foxman, B. M. “Manganese(III)-Based Oxidative Fragmentation-Cyclization Reactions of Unsaturated Cyclobutanols” J. Org. Chem. 1993, 58, 7228-7237. http://dx.doi.org/10.1021/jo00077a054

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151.      Snider, B. B.; McCarthy, B. A. “Ligand, Solvent, and Deuterium Isotope Effects in Mn(III)-Based Oxidative Free-Radical Cyclizations” J. Org. Chem. 1993, 58, 6217-6223. http://dx.doi.org/10.1021/jo00075a015

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150.     Snider, B. B.; McCarthy, B. A. “Oxidative Free-Radical Cyclization of Allylic α-Chloromalonates. Synthesis of (±)-Avenaciolide” Tetrahedron 1993, 49, 9447-9452. http://dx.doi.org/10.1016/S0040-4020(01)80213-1

Oxidative free-radical cyclization of α-chloromalonate 9 with Mn(OAc)3·2H2O and Cu(Oac)2·H2O in acetic acid at 75 °C provides 82% of lactones 10a and 10b. Hydroboration of 10 followed by oxidation affords acids 12, which are converted to avenaciolide precursor 15 in 32% overall yield from 9 by decarboxylation and cyclization.

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149.     Snider, B. B.; Shi, Z. “Biomimetic Synthesis of (±)-Crambines A, B, C1, and C2. Revision of the Structure of Crambines B and C1” J. Org. Chem. 1993, 58, 3828-3839. http://dx.doi.org/10.1021/jo00067a014

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148.     Snider, B. B.; Shi, Z. “Biomimetic Synthesis of the Central Tricyclic Portion of Ptilomycalin A” Tetrahedron Lett. 1993, 34, 2099-2102. http://dx.doi.org/10.1016/S0040-4039(00)60355-6

The central tricyclic portion 20 of ptilomycalin A (1) is formed from bis enone 16 in two steps. Addition of O-methylisourea in DMF to 16 affords a mixture of 17 and 18 that are both converted to a single tricyclic aminal 20a on treatment with NH3 and NH4OAc in methanol at reflux.

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147.      Snider, B. B.; Zhang, Q. “Synthesis of (±)-Okicenone and (±)-Aloesaponol III” J. Org. Chem. 1993, 58, 3185-3187. http://dx.doi.org/10.1021/jo00063a049

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146.     Snider, B. B.; Armanetti, L.; Baggio, R. “Oxidative Free-Radical Cyclization of Dimethyl (4E,8-Nonadien-1-yl)malonate and Ethyl (4E,8-Nonadien-1-yl)cyanoacetate” Tetrahedron Lett. 1993, 34, 1701-1704. http://dx.doi.org/10.1016/S0040-4039(00)60756-6

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145.     Snider, B. B.; Zhang, Q. “Asymmetric Induction in Manganese(III)-Based Oxidative Free-Radical Cyclizations of Chiral Esters and Amides” Tetrahedron Lett. 1992, 33, 5921-5924, http://dx.doi.org/10.1016/S0040-4039(00)61089-4

Mn(III)-based oxidative free-radical cyclizations of phenylmenthyl acetoacetate 1d affords 90% of 11 with 86% de. trans-2-Phenylcyclohexyl ester 1e affords 5e with only 60% de. The 2,5-dimethylpyrrolidine amide 1h affords 14 with higher de (92%), but in only 28% yield.

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144.      Snider, B. B.; Buckman, B. O. “Total Synthesis of (±)-Velloziolone” J. Org. Chem. 1992, 57, 4883-4888. http://dx.doi.org/10.1021/jo00044a024

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143.     Snider, B. B.; Zhang, Q.; Dombroski, M. A. “Control of the Regioselectivity of Oxidative Free-Radical Cyclizations by Addition to Haloalkenes” J. Org. Chem. 1992, 57, 4195-2405. http://dx.doi.org/10.1021/jo00041a026

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142.     Snider, B. B.; Shi, Z. “Biomimetic Synthesis of the Bicyclic Guanidine Moieties of Crambines A and B” J. Org. Chem. 1992, 57, 2526-2568. http://dx.doi.org/10.1021/jo00035a005

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141.      Snider, B. B.; Yang, K. “A Short Enantiospecific Synthesis of the Ceroplastin Nucleus” J. Org. Chem. 1992, 57, 3615-3626. http://dx.doi.org/10.1021/jo00039a021

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140.     Snider, B. B.; Kwon, T. “Oxidative Cyclization of d,e- and e,z-Unsaturated Enol Silyl Ethers and Unsaturated Siloxycyclopropanes” J. Org. Chem. 1992, 57, 2399-2410. http://dx.doi.org/10.1021/jo00034a038

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139.     Snider, B. B. “Intramolecular Cycloadditions of Ketenes and Ketenimium Salts with Alkenes” in Advances in Strain in Organic Chemistry, Vol. 2, B. Halton, Editor; JAI Press, London, 1992, pp 95-142.

138.     Dombroski, M. A.; Snider, B. B. “Manganese(III)-Based Oxidative Free-Radical Cyclizations of γ,γ-Bis(allylic) Acetoacetates” Tetrahedron 1992, 48, 1417-1426. http://dx.doi.org/10.1016/S0040-4020(01)92231-8

Oxidative free-radical cyclizations of γ,γ-(bis)allylic acetoacetates demonstrate that 1,1-disubstituted double bonds are much more reactive than mono- or chloroalkyl-substituted double bonds.

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137.     Snider, B. B.; Shi, Z. “Total Synthesis of (±)-Chondrillin, (±)-Plakorin, and Related Peroxy Ketals. Development of a General Route to 3,6-Dihydro-1,2-dioxin-3-ols” J. Am. Chem. Soc. 1992, 114, 1790-1800. http://dx.doi.org/10.1021/ja00031a038

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136.     Snider, B. B.; Buckman, B. O. “Termination of Manganese(III)-Based Oxidative Free-Radical Cyclizations by Addition to Nitriles. Formation of Cyclopentanones and Cyclohexanones” J. Org. Chem. 1992, 57, 322-326. http://dx.doi.org/10.1021/jo00027a056

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