Recent advances in the synthesis of marine polycyclic ether natural products

Current Opinion in Drug Discovery and Development

Volumn 10, Issue 6, 2007, Pages 784-806

  Fuwa, H ^a   Sasaki, M ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Convergent synthesis; Polycyclic ethers; Synthetic strategies; Total synthesis; Two directional synthesis

Indexed keywords

BREVENAL; BREVETOXIN; CIGUATOXIN; ETHER; GAMBIERIC ACID; NATURAL PRODUCT; POLYCYCLIC ETHER DERIVATIVE; UNCLASSIFIED DRUG;

DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; REVIEW;

ANIMALS; BIOLOGICAL PRODUCTS; CIGUATOXINS; DINOFLAGELLIDA; ETHERS, CYCLIC; MARINE BIOLOGY; MARINE TOXINS; MOLECULAR STRUCTURE; OXOCINS; POLYCYCLIC COMPOUNDS; TECHNOLOGY, PHARMACEUTICAL;

EID: 35948959397     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (72)

1. Yasumoto T, Murata M: Marine toxins. Chem Rev (1993) 93(5):1897-1909.
2. Yasumoto T: The chemistry and biological function of natural marine toxins. Chem Rec (2001) 1(3):228-242.
3. Nakata T: Total synthesis of marine polycyclic ethers. Chem Rev (2005) 105(12):4314-4347. • Provides a comprehensive review of the total synthesis of marine polycyclic ether natural products.
4. Inoue M: Convergent strategies for syntheses of trans-fused polycyclic ethers. Chem Rev (2005) 105(12):4379-4405. • Describes convergent strategies for the synthesis of trans-fused polycyclic ethers and their application to the total synthesis of marine polycyclic ether natural products.
5. Murata M, Legrand AM, Ishibashi Y, Fukui M, Yasumoto Y: Structures and configurations of ciguatoxin from the moray eel Gymnothorax javanicus and its likely precursor from the dinoflagellate Gambierdiscus toxicus. J Am Chem Soc (1990) 112(11):4380- 4386.
6. Satake M, Morohashi A, Oguri H, Oishi T, Hirama M, Harada N, Yasumoto T: The absolute configuration of ciguatoxin. J Am Chem Soc (1997) 119(46):11325-11326.
7. Hirama M, Oishi T, Uehara H, Inoue M, Maruyama M, Oguri H, Satake M: Total synthesis of ciguatoxin CTX3C. Science (2001) 294(5548):1904-1907.
8. Inoue M, Miyazaki K, Uehara H, Maruyama M, Hirama M: First- and second-generation total synthesis of ciguatoxin CTX3C. Proc Natl Acad Sci USA (2004) 101(33):12013-12018.
9. Inoue M, Hirama M: Evolution of a practical total synthesis of ciguatoxin CTX3C. Acc Chem Res (2004) 37(12):961-968.
10. Takizawa A, Fujiwara K, Doi E, Murai A, Kawai H, Suzuki T: Convergent synthesis of the common FGHI-ring part of ciguatoxins. Tetrahedron (2006) 62(31):7408-7435.
11. Fuwa H, Fujikawa S, Tachibana K, Takakura H, Sasaki M: Convergent synthesis of the ABCDE ring fragment of ciguatoxins. Tetrahedron Lett (2004) 45(24):4795-4799.
12. Nonoyama A, Hamajima A, Isobe M: Synthesis of symmetric HIJ-ring model of ciguatoxin. Tetrahedron (2006) 63(26):5886-5894.
13. Inoue M, Miyazaki K, Ishihara Y, Tatami A, Ohnuma Y, Kawada Y, Komano K, Yamashita S, Lee N, Hirama M: Total synthesis of ciguatoxin and 51-hydroxyCTX3C. J Am Chem Soc (2006) 128(29):9352-9354. •• Describes the first total synthesis of ciguatoxin 1B (CTX1B) and its natural congener 51-hydroxy-CTX3C.
14. Inoue M, Wang GX, Wang J, Hirama M: Novel assembly of cyclic ethers by coupling α-chlorosulfides and alcohols. Org Lett (2002) 4(20):3439-3442. • Describes a method for silver(I)-promoted coupling of α-chlorosulfides with alcohols, which is the key fragment assembly process in the total synthesis of CTX and 51-hydroxy-CTX3C from the Hirama group.
15. Kobayashi S, Takahashi Y, Komano K, Alizadeh BH, Kawada Y, Oishi T, Tanaka SI, Ogasawara Y, Sasaki SY, Hirama M: Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C. Tetrahedron (2004) 60(38):8375-8396.
16. Kobayashi S, Alizadeh BH, Sasaki S-Y, Oguri H, Hirama M: Synthesis of the fully functionalized ABCDE ring moiety of ciguatoxin. Org Lett (2004) 6(5):751-754.
17. Nicolaou KC, Bulger PG, Sarlah D: Metathesis reactions in total synthesis. Angew Chem Int Ed (2005) 44(29):4490-4527.
18. Uehara H, Oishi T, Inoue M, Shoji M, Nagumo Y, Kosaka M, Le Brazidec J-Y, Hirama M: Convergent synthesis of the HIJKLM ring fragment of ciguatoxin CTX3C. Tetrahedron (2002) 58(32):6493-6512.
19. Inoue M, Yamashita S, Tatami A, Miyazaki K, Hirama M: A new stereoselective synthesis of ciguatoxin right wing fragments. J Org Chem (2004) 69(8):2797-2804.
20. Mori Y, Yaegashi K, Furukawa H: Oxiranyl anions in organic synthesis: Application to the synthesis of hemibrevetoxin B. J Am Chem Soc (1997) 119(19):4557-4558.
21. Inanaga, J, Hirata K, Saeki H, Katsuki T, Yamaguchi M: A rapid esterification by means of mixed anhydride and its application to large-ring lactonization. Bull Chem Soc Jpn (1979) 52(7):1989-1993.
22. Horikawa Y, Watanabe M, Fujiwara T, Takeda T: New carbonyl olefination using thioacetals. J Am Chem Soc (1997) 119(5):1127-1128.
23. Bourdelais AJ, Jacocks HM, Wright JLC, Bigwarfe PM Jr, Baden DG: A new polyether ladder compound produced by the dinoflagellate Karenia brevis. J Nat Prod (2005) 68(1):2-6.
24. Abraham WM, Bourdelais AJ, Sabater JR, Ahmed A, Lee TA, Serebriakov I, Baden DG: Airway responses to aerosolized brevetoxins in an animal model of asthma. Am J Respir Crit Care Med (2005) 171(1):26-34.
25. Fuwa H, Ebine M, Sasaki M: Total synthesis of the proposed structure of brevenal. J Am Chem Soc (2006) 128(30):9648-9650.
26. Fuwa H, Ebine M, Bourdelais AJ, Baden DG, Sasaki M: Total synthesis, structure revision, and absolute configuration of (-)-brevenal. J Am Chem Soc (2006) 128(51):16989-16999. •• Describes the first total synthesis, structure revision and determination of the absolute configuration of (-)-brevenal.
27. Miyaura N, Suzuki A: Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev (1995) 95(7):2457-2483.
28. Sasaki M, Fuwa H, Inoue M, Tachibana K: New strategy for convergent synthesis of trans-fused polyether frameworks based on palladium-catalyzed Suzuki cross-coupling reaction. Tetrahedron Lett (1998) 39(49):9027-9030.
29. Sasaki M, Fuwa H, Ishikawa M, Tachibana K: A general method for convergent synthesis of polycyclic ethers based on Suzuki cross-coupling: Concise synthesis of the ABCD ring system of ciguatoxin. Org Lett (1999) 1(7):1075-1077.
30. Sasaki M, Fuwa H: Total synthesis of polycyclic ether natural products based on Suzuki-Miyaura cross-coupling. Synlett (2004) (11):1851-1874. • Describes the development of the Suzuki-Miyaura coupling-based convergent strategy for the synthesis of trans-fused polycyclic ethers and its application to the total synthesis of marine polycyclic ether natural products.
31. Fuwa H, Kainuma N, Tachibana K, Sasaki M: Total synthesis of (-)-gambierol. J Am Chem Soc (2002) 124(50):14983-14992.
32. Tsukano C, Ebine M, Sasaki M: Convergent total synthesis of gymnocin-A and evaluation of synthetic analogues. J Am Chem Soc (2005) 127(12):4326-4335.
33. Evans DA, Bartroli J, Shih TL: Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolates. J Am Chem Soc (1981) 103(8):2127-2129.
34. Kadota I, Ohno A, Matsukawa Y, Yamamoto Y: Synthesis of the H ring of gambierol. Tetrahedron Lett (1998) 39(35):6373-6376.
35. Kotsuki H, Kadota I, Ochi M: An efficient method for the alkylation of chiral triflates with alkynyllithium reagents. A highly concise synthesis of (+)-panaxacol. Tetrahedron Lett (1990) 31(32):4609-4612.
36. 2-induced reductive intramolecular cyclization. Tetrahedron (2002) 59(10):1853-1864.
37. Fuwa H, Sasaki M, Tachibana K: Synthetic studies on a marine polyether toxin, gambierol: Stereoselective synthesis of the FGH ring system via B-alkyl Suzuki coupling. Tetrahedron Lett (2000) 41(43):8371-8375.
38. Fuwa H, Sasaki M, Tachibana K: Synthetic studies on a marine polyether toxin, gambierol: Stereoselective synthesis of the EFGH ring system via B-alkyl Suzuki coupling. Tetrahedron (2001) 57(15):3019-3033.
39. Nicolaou KC, Prasad CVC, Hwang C-K, Duggan ME, Veale CA: Cyclizations of hydroxy dithioketals. New synthetic technology for the construction of oxocenes and related medium-ring systems. J Am Chem Soc (1989) 111(14):5321-5330.
40. Fleming I, Newton TW, Roessler F: The silyl-cupration of acetylenes: A synthesis of vinylsilanes. J Chem Soc Perkin Trans 1 (1981):2527-2532.
41. Stamos DP, Taylor AG, Kishi Y: A mild preparation of vinyliodides from vinylsilanes. Tetrahedron Lett (1996) 37(48):8647-8650.
42. Allred GD, Liebeskind LS: Copper-mediated cross-coupling of organostannanes with organic iodides at or below room temperature. J Am Chem Soc (1996) 118(11):2748-2749.
43. Stille JK: The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles. Angew Chem Int Ed (1986) 25(6):508-524.
44. Nicolaou KC, Reddy KR, Skokotas G, Sato F, Xiao X-Y, Hwang C-K: Total synthesis of hemibrevetoxin B and (7aα)-epi-hemibrevetoxin B. J Am Chem Soc (1993) 115(9):3558-3575.
45. Nakanishi K: The chemistry of brevetoxins - a review. Toxicon (1985) 23(3):473-479.
46. Shimizu Y, Chou HN, Bando H, van Duyne G, Clardy J: Structure of brevetoxin-A (GB-1 toxin), the most potent toxin in the Florida red tide organism Gymnodinium breve (Ptychodiscus brevis). J Am Chem Soc (1986) 108(3):514-515.
47. Nicolaou KC, Yang Z, Shi G-Q, Gunzner JL, Agrios KA, Gärtner P: Total synthesis of brevetoxin A. Nature (1998) 392(6673):264-269.
48. Nicolaou KC, Bunnage ME, McGarry DG, Shi S, Somers PK, Wallace PA, Chu X-J, Agrios KA, Gunzner JL, Yang Z: Total synthesis of brevetoxin A: Part 1: First generation strategy and construction of the BCD ring system. Chem Eur J (1999) 5(2):599-617.
49. Crimmins MT, McDougall PJ, Emmitte KA: A convergent coupling strategy for the formation of polycyclic ethers: Stereoselective synthesis of the BCDE fragment of brevetoxin A. Org Lett (2005) 7(18):4033-4036. • Describes a convergent strategy for the synthesis of trans-fused polycyclic ethers based on Horner-Wadsworth-Emmons coupling and cyclodehydration.
50. Crimmins MT, McDougall PJ, Ellis JM: Improved synthesis of the ABCDE fragment of brevetoxin A. Org Lett (2006) 8(18):4079-4082. •• Describes a highly stereocontrolled, convergent synthesis of the ABCD ring fragment of brevetoxin A based on a Horner-Wadsworth-Emmons coupling strategy.
51. Crimmins MT, Zuccarello JL, Cleary PA, Parrish JD: Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A. Org Lett (2006) 8(1):159-162.
52. Crimmins MT, Choy AL: An asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of oxygen heterocycles: An efficient approach to the enantioselective synthesis of (+)-laurencin. J Am Chem Soc (1999) 121(24):5653-5660.
53. Crabtree RH, Felkin H, Fillebeen-Khan T, Morris GE: Dihydridoiridium diolefin complexes as intermediates in homogeneous hydrogenation. J Organomet Chem (1979) 168(2):183-195.
54. Paterson I, Yeung K-S, Smaill JB: The Horner-Wadsworth-Emmons reaction in natural products synthesis. Expedient construction of complex (E)-enones using barium hydroxide. Synlett (1993) (10):774-776.
55. Johnson HWB, Majumder U, Rainier JD: The total synthesis of gambierol. J Am Chem Soc (2005) 127(3):848-849.
56. Nagai H, Torigoe K, Satake M, Murata M, Yasumoto T, Hirota H: Gambieric acids: Unprecedented potent antifungal substances isolated from cultures of a marine dinoflagellate Gambierdiscus toxicus. J Am Chem Soc (1992) 114(3):1102-1103.
57. Nagai H, Murata M, Torigoe K, Satake M, Yasumoto T: Gambieric acids, new potent antifungal substances with unprecedented polyether structures from a marine dinoflagellate Gambierdiscus toxicus. J Org Chem (1992) 57(20):5448-5453.
58. Morohashi A, Satake M, Nagai H, Oshima Y, Yasumoto T: The absolute configuration of gambieric acids A-D, potent antifungal polyethers, isolated from the marine dinoflagellate Gambierdiscus toxicus. Tetrahedron (2000) 56(46):8995-9001.
59. Kadota I, Oguro N, Yamamoto Y: Synthesis of the A ring segment of gambieric acid. Tetrahedron Lett (2001) 42(21):3645-3647.
60. Kadota I, Takamura H, Yamamoto Y: Synthesis of the J ring segment of gambieric acid. Tetrahedron Lett (2001) 42(21):3649-3651.
61. Clark JS, Fessard TC, Wilson C: A concise and stereoselective synthesis of the A-ring fragment of the gambieric acids. Org Lett (2004) 6(11):1773-1776.
62. Roberts SW, Rainier JD: Synthesis of an A-E gambieric acid subunit with use of a C-glycoside centered strategy. Org Lett (2007) 9(11):2227-2230.
63. Sato K, Sasaki M: Studies toward the total synthesis of gambieric acids, potent antifungal polycyclic ethers: Convergent synthesis of the CDEFG-ring system. Org Lett (2005) 7(12):2441-2444.
64. Sato K, Sasaki M: Studies toward the total synthesis of gambieric acids A and C: Convergent assembly of the nonacyclic polyether skeleton. Angew Chem Int Ed (2007) 46(14):2518-2522.
65. Sato K, Sasaki M: Convergent synthesis of the BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ethers. Tetrahedron (2007) 63(26):5977-6003.
66. Fuwa H, Suzuki A, Sato K, Sasaki M: Stereoselective synthesis of the AB-ring fragment of gambieric acid A. Heterocycles (2007) 72:139-144.
67. Clark JS: Construction of fused polycyclic ethers by strategies involving ring-closing metathesis. Chem Commun (2006) (34):3571-3581. • Summarizes the synthetic strategies used for constructing trans-fused polycyclic ethers based on ring-closing metatheses that have been developed by the Clark group.
68. Clark JS, Hamelin O: Synthesis of polycyclic ethers by two-directional double ring-closing metathesis. Angew Chem Int Ed (2000) 39(2):372-374.
69. Clark JS, Kimber MC, Robertson J, McErlean CSP, Wilson C: Rapid two-directional synthesis of the F-J fragment of the gambieric acids by iterative double ring-closing metathesis. Angew Chem Int Ed (2005) 44(38):6157-6162. •• Describes a concise, two-directional synthesis of the FGHIJ-ring framework of gambieric acids based on the Clark ring-closing metathesis strategy.
70. Denmark SE, Guagnano V, Dixon JA, Stolle A: Tandem inter [4 + 2]/intra [3 + 2] cycloadditions of nitroalkenes. 15. The bridged mode (α-tether). J Org Chem (1997) 62(14):4610-4628.
71. Clark JS, Grainger DM, Ehkirch AA-C, Blake AJ, Wilson C: Synthesis of the fused polyether core of hemibrevetoxin B by two-directional ring-closing metathesis. Org Lett (2007) 9(6):1033-1036.
72. Clark JS, Conroy J, Blake AJ: Rapid synthesis of the A-E fragment of ciguatoxin CTX3C. Org Lett (2007) 9(11):2091-2094.