Anion Relay Chemistry (ARC)
Referenced Publications:
Smith, Amos B., III; Boldi, Armen M. Multicomponent Linchpin Couplings of Silyl Dithianes via Solvent-Controlled Brook Rearrangement. Journal of the American Chemical Society (1997), 119(29), 6925-6926.
A. B. Smith, III and S. M. Pitram. Multicomponent Linchpin Couplings of SilyI Dithianes: Synthesis of the Schreiber C(16-18) Trisacetomide Subtarget for Mycoticin A and B. Org. Lett. 1999, 1, 2001-2004.
A. B. Smith, III, V. A. Doughty, Q. Lin, L.-H. Zhuang, M. D. McBriar, A. M. Boldi, W. H. Moser, N. Murase, K. Nakayama, and M. Sobukawa. The Spongistatins: Architecturally Complex Natural Products. Part One: A Formal Synthesis of (+)-Spongistatin 1
Smith, Amos B., III; Lin, Qiyan; Doughty, Victoria A.; Zhuang, Linghang; McBriar, Mark D.; Kerns, Jeffrey K.; Brook, Christopher S.; Murase, Noriaki; Nakayama, Kiyoshi. The spongistatins: architecturally complex natural products. Part two. Synthesis of th
A. B. Smith, III, S. M. Pitram, M. J. Gaunt, and S. A. Kozmin. Dithiane Additions to Vinyl Epoxides: Steric Control Over the SN2 and SN2′ Manifolds. J. Am. Chem. Soc. 2002, 124, 14516-14517.
A. B. Smith, III, S. M. Pitram, and M. J. Fuertes. (+)-Rimocidin Synthetic Studies. Construction of an Advanced C(1-18) Polyol Fragment. Org. Lett. 2003, 5, 2751-2754.
A. B. Smith, III, S. M. Pitram, A. M. Boldi, M. J. Gaunt, C. Sfouggatakis, and W. H. Moser. Multicomponent Linchpin Couplings. Reaction of Dithiane Anions with Terminal Epoxides, Epichlorohydrin, and Vinyl Epoxides: Efficient, Rapid, and Stereocont
A. B. Smith, III, and D.-S. Kim. Multicomponent Linchpin Coupling of Silyl Dithiane Employing an N-Ts Azirdine as a Second Electrophile: Synthesis of (–)-lndolizidine 223 AB. Org. Lett. 2004, 6, 1493-1495.
A. B. Smith, III, and S. M. Pitram. 2-Tetra-Butyldimethylsilyl-1,3–Dithiane. Electronic Encyclopedia of Reagents for Organic Synthesis, ed. L. Paquette, P. Fuchs, D. Crich, and P. Wipf. John Wiley & Sons
A. B. Smith, III, and C. M. Adams. Evolution of Dithiane-Based Strategies for the Construction of Architecturally Complex Natural Products. Acc. of Chem. Res. 2004, 37, 365-377.
A. B. Smith, III and M. O. Duffey. Bifunctional Molecular Linchpins: A Three-Component Coupling Protocol Employing 2-Bromoallyltrimethylsilane. Synlett, 2004, 1363-1366.
A. B. Smith, III and D.-S. Kim. Total Synthesis of the Neotropical Poison Frog (–) Alkaloid 205B. Org. Lett. 2005, 7, 3247-3250.
A. B. Smith, III and M. Xian. Anion Relay Chemistry: An Effective Tactic for Diversity Oriented Synthesis. J. Am. Chem. Soc. 2006, 128, 66-67.
A. B. Smith, III and D.-S. Kim. A General, Convergent Strategy for the Construction of Indolizidine Alkaloids: Total Synthesis of (–)-Indolizidine 223AB and Alkaloid (–)-205B. J. Org. Chem. 2006, 71, 2547-2557.
A. B. Smith, III, M. Xian, and W.-S. Kim. The [1,5]-Brook Rearrangement: An Initial Application in Anion Relay Chemistry. J. Am. Chem. Soc. 2006, 128, 12368-12369.
A. B. Smith, III, D. S. Kim, and M. Xian. Anion Relay Chemistry Extended. Synthesis of a Gorgonian Sesquiterpene. Org. Lett. 2007, 9, 3307-3309.
A. B. Smith, III and D. S. Kim. The Spirastrellolides: Construction of the Southern C(1)-C(25) Fragment Exploiting Anion Relay Chemistry. Org. Lett. 2007, 9, 3311-3314.
A. B. Smith, III, W. S. Kim and W. M. Wuest. Ortho-TMS Benzaldehyde: An Effective Linchpin for Type II Anion Relay Chemistry. Angew. Chem. Int. Ed. 2008, 47, 7082-7086. PMC2756143.
A. B. Smith, III and W. M. Wuest. Evolution of Multi-Component Anion Relay Chemistry (ARC): Construction of Architecturally Complex Natural and Unnatural Products. Chem. Comm. 2008, 5883-5895. PMC2769507.
N. O. Devarie-Baez, W. Kim, A. B. Smith, III and M. Xian. Multicomponent Type II Anion Relay Chemistry (ARC): “One-Pot” Syntheses of 2,3-Disubstituted Furans and Thiophenes. Org. Lett. 2009, 11, 1861-1864. PMC2777545.
A. B. Smith, III, Q. Lin, V. A. Dougherty, L. Zhuang, M. D. McBriar, J. K. Kerns, A. M. Boldi, N. Murase, W. H. Moser, C. S. Brook, C. S. Bennett, K. Nakayama, M. Sobukawa and R. E. L. Trout. Spongipyran Synthetic Studies. Total Synthesis of (+)-Sp
A. B. Smith, III, C. Sfouggatakis, C. A. Risatti, J. B. Sperry, W. Zhu, V. A. Doughty, T. Tomioka, D. B. Gotchev, C. S. Bennett, S. Sakamoto, O. Atasoylu, S. Shirakami, D. Bauer, M. Takeuchi, J. Koyanagi and Y. Sakamoto. Spongipyran Synthetic Studie
A. B. Smith, III, M. A. Foley, S. Dong, and A. Orbin. (+)-Rimocidin Synthetic Studies: Construction of the C(1-27) Aglycone Skeleton. J. Org. Chem., 2009, 74, 5987-6001. PMC2891182.
A. B. Smith, III, W.-S. Kim and R. Tong. Uniting Anion Relay Chemistry with Pd-Mediated Cross Coupling: Design and Evaluation of Bifunctional Aryl and Vinyl Silane Linchpins. Org. Lett. 2010, 12, 588-591. PMC2813984
A. B. Smith, III and R. Tong. Benzyl and Phenylthiomethyl Silanes: A New Class of Bifunctional Linchpins for Type II Anion Relay Chemistry (ARC). Org. Lett. 2010, 12, 1260-1263. PMC2844645
A. B. Smith, III, H. Smits and D.-S. Kim. Spirastrellolide Studies. Synthesis of the C(1)-C(25) Southern Hemisphere of Spirastrellolides A and B, Exploiting Anion Relay Chemistry. Tetrahedron 2010, 66, 6597-6605. PMC2915457.
A. B. Smith, III and W.-S. Kim. Diversity Oriented Synthesis Leads to a New Class of Bi-functional Linchpins Uniting Anion Relay Chemistry (ARC) with Benzyne Reactivity. Proc. Nat. Acad. Sci. 2011, 108, 6787-6792. PMC3084103.
