Barry Snider, Department Chair
Edison-Lecks 225

Complete Publication List

Barry Snider


Barry Snider

Charles A. Breskin Professor of Organic Chemistry and Department Chair
Ph.D., Harvard University

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 on 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 ,11guanacastepene 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

Figure 1

Figure 2

More recently completed 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),27 juliprosine (27),26 symbioimine (28),28 thallusin (29)29 polygalolide A (30),30 platensimycin (31),31 berkelic acid (32),32 chaetominine (33),33 vibralactone (34)34 and 7-epineoptilocaulin (35).35

Figure 3 

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.36A highlight of recent studies is the tetracyclization of 36 to give 35% of crystalline 37, which was converted to isosteviol (38).37Current studies involve asymmetric induction, extending the scope of the oxidizable substrate, and applications to natural product synthesis.

Figure 4 

Sample of Recent Publications

The link will open a copy of the paper if have a subscription to the journal.

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. http:/

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.     Duvall, J. R.; Wu, F.; Snider, B. B. “Structure Reassignment and Synthesis of Jenamidines A1/A2, Synthesis of (+)-NP25302, and Formal Synthesis of SB-311009 Analogues” J. Org. Chem. 2006, 71, 8579-8590.

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.; Zhou, J. “Synthesis of (+)-Sch 642305 by a Biomimetic Transannular Michael Reaction” Org. Lett. 2006, 8, 1283-1286.

28.     Zhu, Y.; Che, Q.; Snider, B. B. “Total Synthesis of (±)-Symbioimine” Org. Lett. 2006, 8, 5605-5608.

29.     Gao, X.; Matsuo, Y.; Snider, B. B. “Synthesis of ent-Thallusin” Org. Lett. 2006, 8, 2123-2126 and 2007, 9, 379 and

30.     Snider, B. B.; Wu, X.; Nakamura, Hashimoto, S. “A Short, Formal, Biomimetic Synthesis of (±)-Polygalolides A and B” Org. Lett. 2007, 9, 873-874.

31.     Zou, Y.; Chen, C.-H.; Taylor, C. D.; Foxman, B. M.; Snider, B. B. “Formal Synthesis of (±)-Platensimycin” Org. Lett. 2007, 9, 1825-1828.

32.     (a)Zhou, J.; Snider, B. B. “Biomimetic Synthesis of the Tetracyclic Core of Berkelic Acid” Org. Lett. 2007, 9, 2071-2074.
          (b) Wu, X.; Zhou, J.; Snider, B. B. "Synthesis of (-)-Berkelic Acid" Angew. Chem. Int. Ed. 2009, 48, 1283-1286.

33.     Snider, B. B.; Wu, X. “Synthesis of (-)-Chaetominine” Org. Lett. 2007, 9, 4913-4915.

34.     Zhou, Q.; Snider, B. B. “Synthesis of (±)-Vibralactone” Org. Lett. 2008, 10, 1401-1404.  Zhou, Q.; Snider, B. B. “Synthesis of (±)- and (-)-Vibralactone and Vibralactone C” J. Org. Chem. 2008, 72, ASAP.

35.     Yu. M.; Pochapsky, S. S.; Snider. B. B. "Synthesis of 7-Epineoptilocaulin, Mirabilin B, and Isoptilocaulin.  A Unified Biosynthetic Proposal for the Ptilocaulin and Batzelladine Alkaloids.  Synthesis and Structure Revision of Netamines E and G" J. Org. Chem. 2008, 72, ASAP.

36.     Snider, B. B. “Manganese(III)-Based Oxidative Free-Radical Cyclizations” Chem. Rev. 1996, 96, 339-363.

37.     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.