Keywords

Enter a program, idea, office, or department into the field above and click go

Barry B. Snider

Charles A. Breskin Professor of Organic Chemistry
Ph.D., Harvard University (1973)
office 781-736-2550
fax 781-736-2516
snider@brandeis.edu

Complete Publication List

Our main focus is the total synthesis of biologically active natural products.  We also work on the development of new free-radical based synthetic methods.  In optimal cases new methods are developed and applied to the synthesis of biologically active natural products.

Total Synthesis. Targets are chosen based the biological activity of the target and the structural novelty of the ring system or functionality. In the past few years we have completed syntheses of the structurally novel potent heptatoxin cylindrospermopsin (1),1 the immunosuppressant FR901483 (2),2 antimuscarinic agents in the TAN1251 series (3),3 the neurotoxin dysiherbaine (4),4 the CCK antagonist asperlicin (5),5 the pentacyclic core of ptilomycalin A (6),6 the anti AIDS tricyclic guanidine batzelladine E (7),7 the bradykinin antagonist cycloanchinopeptolide D (8),8 the nerve growth factor stimulant erinacine A (9),9 unusual tricyclic alkaloids in the cylindricine A (10) family,10 fumiquinazolines A, B, C (11), E, H, and I ,11 guanacastepene A (12),12 martinellic acid (13),13 dysibetaine (14),14 salicylihalamide A (15),15 pyrinodemin A (16),16 waol A (18),17 and phloeodictine A1 (17).18

Recently completed and ongoing targets include haterumalide (19),19 cladybotryal (20),20 cytoskyrin A (21) analogues,21 epohelmin A (22),22 jenamidines A1/A2 (23),23 vaginol and vagindiol (24ab),24 abyssomicin C (25),25 Sch 642305 (26), and juliprosine (27).26

Methods Development.  Oxidative free-radical cyclizations, in which the initial radical is generated oxidatively, and/or the cyclic radical is oxidized to terminate the reaction, have considerable synthetic potential since more highly functionalized products can be prepared from simpler precursors than with standard tin hydride reductive radical cyclizations.  Over the past 15 years we have developed the use of Mn(OAc)3, often in conjunction with Cu(OAc)2, for the oxidative cyclization of unsaturated ketones and 1,3-dicarbonyl compounds.27  A highlight of recent studies is the tetracyclization of 28 to give 35% of crystalline 29, which was converted to isosteviol (30).28  Current studies involve asymmetric induction, extending the scope of the oxidizable substrate, and applications to natural product synthesis.


References:

  1. Xie, C.; Runnegar, M. T. C.; Snider, B. B. “Total Synthesis of (±)-Cylindrospermopsin” J. Am. Chem. Soc. 2000, 122, 5017-5024.
  2. Snider, B. B.; Lin, H. “Total Synthesis of (-)-FR901483” J. Am. Chem. Soc. 1999, 121, 7778-7786.
  3. Snider, B. B.; Lin, H. “Biomimetic Total Syntheses of (-)-TAN1251A, (+)-TAN1251B, (+)-TAN1251C, and (+)-TAN1251D” Organic Letters, 2000, 2, 643-646.
  4. Snider, B. B.; Hawryluk, N. A. “Synthesis of (-)-Dysiherbaine” Organic Letters, 2000, 2, 635-638.
  5. He, F.; Foxman, B. M.; Snider, B. B. “Total Syntheses of (-)-Asperlicin and (-)-Asperlicin C” J. Am. Chem. Soc. 1998, 120, 6417-6418.
  6. Snider, B. B.; Shi, Z. “Biomimetic Synthesis of the Pentacyclic Nucleus of Ptilomycalin A” J. Am. Chem. Soc. 1994, 116, 549-557.
  7. Snider, B. B.; Chen, J. “Synthesis of Batzelladine E and its E Isomer” Tetrahedron Lett. 1998, 39, 5697-5700.
  8. Snider, B. B.; Song, F.; Foxman, B. M. “Total Syntheses of (±)-Anchinopeptolide D and (±)-Cycloanchinopeptolide D” J. Org. Chem. 2000, 65, 793-800.
  9. Snider, B. B.; Vo, N. H.; O'Neil, S. V. “Synthesis of (±)-Allocyathin B2 and (+)-Erinacine A” J. Org. Chem. 1998, 63, 4732-4740.
  10. Snider, B. B.; Liu, T. “Synthesis of (±)-Cylindricines A, D, and E” J. Org. Chem. 1997, 62, 5630-5633.
  11. Snider, B. B.; Zeng, H. “Total Syntheses of (-)-Fumiquinazolines A, B, C, E, H, and I. Approaches to the Synthesis of Fiscalin A.” J. Org. Chem. 2003, 68, 545-563.
  12. Shi, B.; Hawryluk, N. A.; Snider, B. B. “Formal Synthesis of (±)-Guanacastepene” J. Org. Chem. 2003, 68, 1030-1042.
  13. Snider, B. B.; Ahn, Y.; O’Hare, S. “Total Synthesis of (±)-Martinellic Acid” Org. Lett. 2001, 3, 4217-4220.
  14. Snider, B. B.; Gu, Y.-H. “Total Synthesis of (-)- and (+)-Dysibetaine” Org. Lett. 2001, 3, 1761-1763.
  15. Snider, B. B.; Song, F. “Total Synthesis of (-)-Salicylihalamide A” Org. Lett. 2001, 3, 1817-1820.
  16. Snider, B. B.; Shi, B. “Synthesis of pyrinodemins A and B. Assignment of the double bond position of pyrinodemin A” Tetrahedron Lett. 2001, 40, 139-1642.
  17. Gao, X.; Snider, B. B. “Syntheses of (-)-TAN-2483A, (-)-Massarilactone B, and the Fusidilactone B Ring System.  Revision of the Structures of and Syntheses of (±)-Waol A (FD-211) and (±)-Waol B (FD-212)” J. Org. Chem. 2004, 69, 5517-5527.
  18. Neubert, B. J.; Snider, B. B. “Synthesis of (±)-Phloeodictine A1” Org. Lett. 2003, 5, 765-768.
  19. Gu, Y.; Snider, B. B. “Synthesis of ent-Haterumalide NA (ent-Oocydin A) Methyl Ester” Org. Lett. 2003, 5, 4385-4388.
  20. Snider, B. B.; Che, Q. “Synthesis of Cladobotryal, CJ16,169 and CJ16,170” Org. Lett. 2004, 6, 2877-2880. 248.
  21. Snider, B. B.; Gao, X. “Efficient Syntheses of Rugulosin Analogues” J. Org. Chem. 2005, 70, 6863-6869.
  22. Snider, B. B.; Gao, X. “Structure Revision and Syntheses of Epohelmins A and B” Org. Lett. 2005, 7, 4419-4422.
  23. Snider, B. B.; Duvall, J. R. “Synthesis of Jenamidines A1/A2” Org. Lett. 2005, 7, 4519-4522.
  24. Zou, Y.; Lobera, M.; Snider, B. B. “Synthesis of 2,3-Dihydro-3-hydroxy-2-hydroxylalkylbenzofurans from Epoxy Aldehydes.  One-step Syntheses of Brosimacutin G, Vaginidiol, Vaginol, Smyrindiol, Xanthoarnol, and Avicenol A.  Biomimetic Syntheses of Angelicin and Psoralen” J. Org. Chem. 2005, 70, 1761-1770.
  25. Snider, B. B. Zou, Y. F. “Synthesis of the Carbocyclic Skeleton of Abyssomicins C and D” Org. Lett. 2005, 7, 4939-4941.
  26. Snider, B. B.; Neubert, B. J. “Syntheses of Ficusceptine, Juliprosine, and Juliprosopine by Biomimetic Intramolecular Chichibabin Pyridine Syntheses” Org. Lett. 2005, 7, 2715-2718.
  27. Snider, B. B. “Manganese(III)-Based Oxidative Free-Radical Cyclizations” Chem. Rev. 1996, 96, 339-363.
  28. Snider, B. B.; Kiselgof, J. Y.; Foxman, B. M. “Total Syntheses of (±)-Isosteviol and (±)-Beyer-15-ene-3b,19-diol by Manganese(III)-Based Oxidative Quadruple Free-Radical Cyclization” J. Org. Chem. 1998, 63, 7945-7952.