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173. Cho, T. H.; Chaudhuri, B.; Snider, B. B.; Foxman, B. M. “Stereospecific g-Ray-Induced Dimerization of Crystalline Bis(trans-butenoato)calcium” Chem. Commun. 1996, 1337-1338. http://dx.doi.org/10.1039/CC9960001337
Irradiation (60Co γ-rays) of crystalline bis(trans-but-2-enoato)calcium induces a unique solid-state cyclodimerization reaction; the product, cis,trans-nepetic acid (6), is one of four possible diastereomers
172. Cole, B. M.; Han, L.; Snider, B. B. “Mn(III)-Based Oxidative Free-Radical Cyclizations of Unsaturated Ketones” J. Org. Chem. 1996, 61, 7832-7847. http://dx.doi.org/10.1021/jo961199u
171. Snider, B. B.; Chen, J. “Synthesis of the Tricyclic Portions of Batzelladines A, B and D. Revision of the Stereochemistry of Batzelladines A and D” Tetrahedron Lett. 1996, 37, 6977-6980. http://dx.doi.org/10.1016/0040-4039(96)01575-4
170. Snider, B. B.; Vo, N. H.; O’Neil, S. V.; Foxman, B. M. “Synthesis of (±)-Allocyathin B2 and (+)-Erinacine A” J. Am. Chem. Soc. 1996, 118, 7644-7645. http://dx.doi.org/10.1021/ja9615379
169. Snider, B. B. “Manganese(III)-Based Oxidative Free-Radical Cyclizations” Chem. Rev. (Washington, D. C.) 1996, 96, 339-363. http://dx.doi.org/10.1021/cr950026m
168. Snider, B. B.; Kiselgof, E. Y. “Mn(III)-Based Oxidative Free Radical Cyclizations of Unsaturated 2-Cyclohexenones and Aldehydes” Tetrahedron 1996, 52, 6073-6084. http://dx.doi.org/10.1016/0040-4020(96)00234-7
167. Snider, B. B.; Lu, Q. “Total Synthesis of (±)-Leporin A” J. Org. Chem. 1996, 61, 2839-2844. http://dx.doi.org/10.1021/jo952053i
166. Snider, B. B.; O’Neil, S. V. “Formal Synthesis of (±)-Upial. Oxidative Free-Radical Cyclization of Unsaturated 1,3-Cyclohexanediones” Tetrahedron 1995, 51, 12983-12994. http://dx.doi.org/10.1016/0040-4020(95)00841-U
Oxidative free-radical cyclization of 4-(3-hexenyl)-4,5-dimethyl-1,3-cyclohexanedione (8) affords 85% of a diastereomeric mixt. of bicyclic dione 7. Short sequences were developed to convert this mixt. to carboxylate 2, a late intermediate in Taschner’s synthesis of upial.
165. Snider, B. B. “Thermal [2 + 2] Cycloadditions” in Methoden der Organische Chemie (Houben-Weyl) Vol. E21C; Georg Thieme Verlag, Stuttgart, 1995, Chapter 18.104.22.168.
164. Snider, B. B.; Han, L. “Formation of 2,2-Dichloro-1-Tetralones by Oxidative Free-Radical Annulation” Synth. Commun. 1995, 25, 2337-2347. http://dx.doi.org/10.1080/00397919508011791
Oxidative free-radical annulation of dichloroacetophenone with terminal alkenes provides modest to good yields of 4-substituted 2,2-dichloro-l-tetralones (10), whose synthetic utility and reactivity is described.
163. Snider, B. B.; Cole, B. M. “Mn(III)-Based Oxidative Free Radical Cyclization of Unsaturated Ketones” J. Org. Chem. 1995, 60, 5376-5377. http://dx.doi.org/10.1021/jo00122a006
162. Snider, B. B.; Harvey, T. C. “Synthesis of a Bicyclic Model for the Marine Hepatotoxin Cylindrospermopsin” Tetrahedron Lett. 1995, 36, 4587-4590. http://dx.doi.org/10.1016/0040-4039(95)00872-A
161. Snider, B. B.; O’Neil, S. “Synthesis of (-)-Acetylsaturejol and (+)-Isoacetylsaturejol” Synth. Commun. 1995, 25, 1085-1091. http://dx.doi.org/10.1080/00397919508012671
(−)-Acetylsaturejol (11) and (+)-isoacetylsaturejol (12a) have been prepared from (−)-cis-4-acetoxypulegone (10) by photosensitized singlet oxygen and non-singlet oxygen addition, respectively.
160. Snider, B. B.; McCarthy, B. A. “Mn(III)-Mediated Electrochemical Oxidative Free-Radical Cyclizations” in Benign by Design, Alternative Synthetic Design for Pollution Prevention, ACS Symposium Series 577, Editors, P. A. Anastas and C. A. Ferris, American Chemical Society, Washington, D. C. 1994, pp 84-97. http://dx.doi.org/10.1021/bk-1994-0577.ch007
Mn(III)-based oxidative free-radical cyclizations and addns. are versatile reactions that have been extensively developed over the past decade allowing free-radical cyclizations to be carried out without toxic tin reagents. Their applicability in large scale synthesis is limited by the requirement for ≥2 equiv of Mn(OAc)3 per mol of substrate oxidized. While manganese is not expensive, it is toxic, and the disposal of large quantities poses a pollution problem. A variety of procedures were investigated to develop a cheap and safe method for reoxidizing Mn(II) to Mn(III) during the oxidn. of the org. substrate. Successful results in some cases were obtained using anodic oxidn. to reoxidize Mn(II) to Mn(III) in a mixed solvent of AcOH and EtOH contg. NaOAc as an electrolyte. Sodium periodate in DMSO is also capable of reoxidizing Mn(II) to Mn(III).
159. Snider, B. B.; Lu, Q. “Total Synthesis of (±)-Pyridoxatin (1)” J. Org. Chem. 1994, 59, 8065-8070. http://dx.doi.org/10.1021/jo00105a024
158. Vo, N. H.; Snider, B. B. “Total Synthesis of (-)-Silphiperfol-6-ene and (-)-Methyl Cantabradienate” J. Org. Chem. 1994, 59, 5419-5423. http://dx.doi.org/10.1021/jo00097a053
157. Snider, B. B.; Shi, Z.; O’Neil, S. V.; Kreutter, K. D.; Arakaki, T. L. “Stereochemical Dependence of Base-Catalyzed Cleavage of Cyclic Peroxy Ketals” J. Org. Chem. 1994, 59, 1726-1729. http://dx.doi.org/10.1021/jo00086a022
156. Snider, B. B.; Harvey, T. C. “Conversion of a 2,5,7-Nonatrien-4-one to a Bicyclo[4.2.0]octenone by a Series of Electrocyclic Reactions” J. Org. Chem. 1994, 59, 504-506. http://dx.doi.org/10.1021/jo00081a040
155. Snider, B. B.; Shi, Z. “Biomimetic Synthesis of the Pentacyclic Nucleus of Ptilomycalin A” J. Am. Chem. Soc. 1994, 116, 549-557. http://dx.doi.org/10.1021/ja00081a015
154. Snider, B. B.; Lu, Q. “A Two-Step Synthesis of Pyridoxatin Analogs” Tetrahedron Lett. 1994, 35, 531-534. http://dx.doi.org/10.1016/S0040-4039(00)75830-8