CONTACT INFORMATION

Barry Snider, Department Chair
Edison-Lecks 225
781-736-2550
snider@brandeis.edu

Complete Publication List

Barry Snider

snider-b3.jpg

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. http://dx.doi.org/10.1021/ja000647j

2.       Snider, B. B.; Lin, H. “Total Synthesis of (-)-FR901483” J. Am. Chem. Soc. 1999, 121, 7778-7786. http://dx.doi.org/10.1021/ja991160h

3        Snider, B. B.; Lin, H. “Biomimetic Total Syntheses of (-)-TAN1251A, (+)-TAN1251B, (+)-TAN1251C, and (+)-TAN1251D” Organic Letters, 2000, 2, 643-646. http://dx.doi.org/10.1021/ol991401q

4.       Snider, B. B.; Hawryluk, N. A. “Synthesis of (-)-Dysiherbaine” Organic Letters, 2000, 2, 635-638. http://dx.doi.org/10.1021/ol991393d

5.       He, F.; Foxman, B. M.; Snider, B. B. “Total Syntheses of (-)-Asperlicin and (-)-Asperlicin C” J. Am. Chem. Soc. 1998, 120, 6417-6418. http://dx.doi.org/10.1021/ja9809408

6.       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

7.       Snider, B. B.; Chen, J. “Synthesis of Batzelladine E and its E Isomer” Tetrahedron Lett. 1998, 39, 5697-5700. http://dx.doi.org/10.1016/S0040-4039(98)01196-4

8.       Snider, B. B.; Song, F.; Foxman, B. M. “Total Syntheses of (±)-Anchinopeptolide D and (±)-Cycloanchinopeptolide D” J. Org. Chem. 2000, 65, 793-800. http://dx.doi.org/10.1021/jo991454l

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. http://dx.doi.org/10.1021/jo9804700

10.     Snider, B. B.; Liu, T. “Synthesis of (±)-Cylindricines A, D, and E” J. Org. Chem. 1997, 62, 5630-5633. http://dx.doi.org/10.1021/jo970536b

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. http://dx.doi.org/10.1021/jo0264980

12.     Shi, B.; Hawryluk, N. A.; Snider, B. B. “Formal Synthesis of (±)-Guanacastepene” J. Org. Chem. 2003, 68, 1030-1042. http://dx.doi.org/10.1021/jo026702j

13.     Snider, B. B.; Ahn, Y.; O’Hare, S. “Total Synthesis of (±)-Martinellic Acid” Org. Lett. 2001, 3, 4217-4220. http://dx.doi.org/10.1021/ol016884o

14.     Snider, B. B.; Gu, Y.-H. “Total Synthesis of (-)- and (+)-Dysibetaine” Org. Lett. 2001, 3, 1761-1763. http:/dx.doi.org/10.1021/ol015954o

15.     Snider, B. B.; Song, F. “Total Synthesis of (-)-Salicylihalamide A” Org. Lett. 2001, 3, 1817-1820. http://dx.doi.org/10.1021/ol015822v

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. http://dx.doi.org/10.1016/S0040-4039(01)00003-X

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. http://dx.doi.org/10.1021/jo0358628

18.     Neubert, B. J.; Snider, B. B. “Synthesis of (±)-Phloeodictine A1” Org. Lett. 2003, 5, 765-768.  http://dx.doi.org/10.1021/ol034042e

19.     Gu, Y.; Snider, B. B. “Synthesis of ent-Haterumalide NA (ent-Oocydin A) Methyl Ester” Org. Lett. 2003, 5, 4385-4388. http://dx.doi.org/10.1021/ol0356789

20.     Snider, B. B.; Che, Q. “Synthesis of Cladobotryal, CJ16,169 and CJ16,170” Org. Lett. 2004, 6, 2877-2880. 248. http://dx.doi.org/10.1021/ol049130t

21.     Snider, B. B.; Gao, X. “Efficient Syntheses of Rugulosin Analogues” J. Org. Chem. 2005, 70, 6863-6869. http://dx.doi.org/10.1021/jo0508898

22.     Snider, B. B.; Gao, X. “Structure Revision and Syntheses of Epohelmins A and B” Org. Lett. 2005, 7, 4419-4422. http://dx.doi.org/10.1021/ol0516061

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. http://dx.doi.org/10.1021/jo061650%2B

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. http://dx.doi.org/10.1021/jo047974k

25.     Snider, B. B. Zou, Y. F. “Synthesis of the Carbocyclic Skeleton of Abyssomicins C and D” Org. Lett. 2005, 7, 4939-4941. http://dx.doi.org/10.1021/ol0518941

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. http://dx.doi.org/10.1021/ol050931l

27.     Snider, B. B.; Zhou, J. “Synthesis of (+)-Sch 642305 by a Biomimetic Transannular Michael Reaction” Org. Lett. 2006, 8, 1283-1286. http://dx.doi.org/10.1021/ol052948%2B

28.     Zhu, Y.; Che, Q.; Snider, B. B. “Total Synthesis of (±)-Symbioimine” Org. Lett. 2006, 8, 5605-5608. http://dx.doi.org/10.1021/ol062333s

29.     Gao, X.; Matsuo, Y.; Snider, B. B. “Synthesis of ent-Thallusin” Org. Lett. 2006, 8, 2123-2126 and 2007, 9, 379http://dx.doi.org/10.1021/ol0605777%20 and http://dx.doi.org/10.1021/ol062970i

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. http://dx.doi.org/10.1021/ol0630898

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. http://dx.doi.org/10.1021/ol070563g

32.     (a)Zhou, J.; Snider, B. B. “Biomimetic Synthesis of the Tetracyclic Core of Berkelic Acid” Org. Lett. 2007, 9, 2071-2074. http://dx.doi.org/10.1021/ol0704338
          (b) Wu, X.; Zhou, J.; Snider, B. B. "Synthesis of (-)-Berkelic Acid" Angew. Chem. Int. Ed. 2009, 48, 1283-1286. http://dx.doi.org/10.1002/ange.200805488

33.     Snider, B. B.; Wu, X. “Synthesis of (-)-Chaetominine” Org. Lett. 2007, 9, 4913-4915. http://dx.doi.org/10.1021/ol7022483

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. http://dx.doi.org/10.1021/jo8015743

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. http://dx.doi.org/10.1021/jo801956w

36.     Snider, B. B. “Manganese(III)-Based Oxidative Free-Radical Cyclizations” Chem. Rev. 1996, 96, 339-363. http://dx.doi.org/10.1021/cr950026m

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. http://dx.doi.org/10.1021/jo981238x