Syntheses of methylenolactocin and nephrosterinic acid via diastereoselective acylation and chemoselective reduction-lactonization

Tetrahedron

Volumn 65, Issue 32, 2009, Pages 6382-6389

  Jongkol, Rattana ^a   Choommongkol, Ruangrat ^a   Tarnchompoo, Bongkoch ^b   Nimmanpipug, Piyarat ^a   Meepowpan, Puttinan ^a  

^a CHIANG MAI UNIVERSITY   (Thailand)

^b NATIONAL SCIENCE AND TECHNOLOGY DEVELOPMENT AGENCY   (Thailand)

Author keywords

Methylene butyrolactones; Acylation; Lactonization; Reduction

Indexed keywords

LACTONE DERIVATIVE; METHYLENOLACTOCIN; NEPHROSTERINIC ACID; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED RADIATION; LACTONIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 67649840195     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.016     Document Type: Article

References (86)

1. Mori K., and Yamane K. Tetrahedron 38 (1982) 2919-2921
2. Hoffmann H.M.R., and Rabe J. Angew. Chem., Int. Ed. Engl. 24 (1985) 94-110 and references cited therein
3. Petragnani N., Ferraz H.M.C., and Silva G.V.J. Synthesis (1986) 157-183
4. Sibi M.P., Deshpande P.K., and La Loggia A.J. Synlett (1996) 343-345 and references cited therein
5. Park B.K., Nakagawa M., Hirota A., and Nakayama M. Agric. Biol. Chem. 51 (1987) 3443-3444
6. Park B.K., Nakagawa M., Hirota A., and Nakayama M. J. Antibiot. 41 (1988) 751-758
7. Nakayama, M.; Nakagawa, S.; Boku, T.; Hirota, A.; Shima, S.; Nakanishi, O.; Yamada, Y. Jpn. Kokai Tokkyo Koho 1989, JP 01016776 A, 20/01/1989;
8. Chem. Abstr. 112 (1990) 34404f
9. For total and formal syntheses of methylenolactocin:
10. Carlson R.M., and Oyler A.R. J. Org. Chem. 41 (1976) 4065-4069
11. Honda T., and Kimura N. J. Chem. Soc., Chem. Commun. (1994) 77-78
12. Takahata H., Uchida Y., and Momose T. J. Org. Chem. 60 (1995) 5628-5633
13. Vaupel A., and Knochel P. Tetrahedron Lett. 36 (1995) 231-232
14. Mawson S.D., and Weavers R.T. Tetrahedron 51 (1995) 11257-11270
15. Zhu G., and Lu X. Tetrahedron: Asymmetry 6 (1995) 885-892
16. Zhu G., and Lu X. J. Org. Chem. 60 (1995) 1087-1089
17. Drioli S., Felluga F., Forzato C., Nitti P., and Pitacco G. Chem. Commun. (1996) 1289-1290
18. Saicic R.N., and Zard S.Z. Chem. Commun. (1996) 1631-1632
19. Sarkar S., and Ghosh S. Tetrahedron Lett. 37 (1996) 4809-4810
20. Ghatak A., Sarkar S., and Ghosh S. Tetrahedron 53 (1997) 17335-17342
21. Chandrasekharam M., and Liu R.S. J. Org. Chem. 63 (1998) 9122-9124
22. Mandal P.K., Maiti G., and Roy S.C. J. Org. Chem. 63 (1998) 2829-2834
23. Lertvorachon J., Meepowpan P., and Thebtaranonth Y. Tetrahedron 54 (1998) 14341-14358
24. Masaki Y., Arasaki H., and Itoh A. Tetrahedron Lett. 40 (1999) 4829-4832
25. Forbes J.E., Saicic R.N., and Zard S.Z. Tetrahedron 55 (1999) 3791-3802
26. Loh T.P., and Lye P.L. Tetrahedron Lett. 42 (2001) 3511-3514
27. Kongsaeree P., Meepowpan P., and Thebtaranonth Y. Tetrahedron: Asymmetry 12 (2001) 1913-1922
28. Ariza X., Garcia J., Lopez M., and Montserrat L. Synlett (2001) 120-122
29. Felluga F., Fermeglia M., Ferrone M., Pitacco G., Pricl S., and Valentin E. Helv. Chim. Acta 85 (2002) 4046-4054
30. Chhor R.B., Nosse B., Sorgel S., Bohm C., Seitz M., and Reiser O. Chem.-Eur. J. 9 (2003) 260-270
31. Ariza X., Fernandez N., Garcia J., Lopez M., Montserrat L., and Ortiz J. Synthesis (2004) 128-134
32. Hon Y.-S., Hsieh C.-H., and Liu Y.-W. Tetrahedron 61 (2005) 2713-2723
33. Braukmueller S., and Brueckner R. Eur. J. Org. Chem. (2006) 2110-2118
34. Blanc D., Madec J., Popowyck F., Ayad T., Phansavath P., Ratovelomanana-Vidal V., and Genet J.-P. Adv. Syn. Catal. 349 (2007) 943-950
35. Hajra S., Karmakar A., Giri A.K., and Hazra S. Tetrahedron Lett. 49 (2008) 3625-3627
36. Asahina Y., Yanagita M., and Sakurai Y. Chem. Ber. 70B (1937) 227-235
37. For total syntheses of nephrosterinic acid, see: Refs. 4a, d, n and r.
38. Zopf W. Liebigs Ann. Chem. 324 (1902) 39-78
39. Asahina Y., and Asano M. J. Pharm. Sci. Jpn. 539 (1927) 1-17
40. Asahina Y., and Yanagita M. Chem. Ber. 69B (1936) 120-125
41. For total and formal syntheses of protolichesterinic acid:
42. Van Tamelen E.E., and Bach S.R. J. Am. Chem. Soc. 80 (1958) 3079-3086
43. Loffler A., Pratt R.D., Pucknat J., Gelbard G., and Dreiding A.S. Chimica 23 (1969) 413-416
44. Martin J., Watts P.C., and Johnson F. J. Org. Chem. 39 (1974) 1676-1681
45. Damon R.E., and Schlessinger R.H. Tetrahedron Lett. 17 (1976) 1561-1564
46. Chen M.J., and Liu R.S. Tetrahedron Lett. 39 (1998) 9465-9468
47. Murta M.M., de Azevedo M.B.M., and Greene A.E. J. Org. Chem. 58 (1993) 7537-7541
48. Martin T., Rodriguez C.M., and Martin V.S. J. Org. Chem. 61 (1996) 6450-6453
49. See Refs. 4a, k, m, n and o.
50. Bérdy J. Handbook of Antibiotic Compounds Vol. IX (1982), CRC, Boca Raton, FL and references cited therein
51. Cavallito C.J., Fruehuauf McK.D., and Bailey J.N. J. Am. Chem. Soc. 70 (1948) 3724-3726
52. Shibata S., Miura Y., Sugimura H., and Toyoizumi Y. Yakugaku Zasshi 68 (1948) 300-303
53. Chem. Abstr. 45 (1951) 6691i
54. Fujikawa F., Hitosa Y., Yamaoka M., Fujiwara Y., Nakazawa S., Omatsu T., and Toyoda T. Yakugaku Zasshi 73 (1953) 135-138
55. Chem. Abstr. 48 (1954) 230a
56. Borkawski B., Wozniak W., Gertig H., and Werakso B. Diss. Pharm. 16 (1964) 189-194
57. Chem. Abstr. 62 (1965) 1995b
58. Sticker O. Pharm. Acta Helv. 40 (1965) 483-495
59. Chem. Abstr. 63 (1965) 8778d
60. Sticker O. Pharm. Acta Helv. 40 (1965) 385-394
61. Chem. Abstr. 63 (1965) 12026c
62. Hirayama T., Fujikawa F., Kasahara T., Otsuka M., Nishida N., and Mizuno D. Yakugaku Zasshi 100 (1980) 755-759
63. Chem. Abstr. 93 (1980) 179563f
64. Ingolfsdottir K., Hjalmarsdottir M., Sigurdsson A., Gudjonsdottir G.A., Brynjolfsdottir A., and Steingrimsson O. Antimicrob. Agents Chemother. 41 (1997) 215-217
65. Ingolfsdottir K., Chung G.A.C., Skulason V.G., Gissurarson S.R., and Vilhelmsdottir M. Eur. J. Pharm. Sci. 6 (1998) 141-144
66. Turk A.O., Yilmaz M., Kivanc M., and Turk H. Z. Naturforsch. C 58 (2003) 850-854
67. Hughes M.A., McFadden J.M., and Townsend C.A. Bioorg. Med. Chem. Lett. 15 (2005) 3857-3859
68. Freysdottir J., Omarsdottir S., Ingolfsdottir K., Vikingsson A., and Olafsdottir E.S. Int. Immunopharmacol. 8 (2008) 423-430
69. Bucar F., Schneider I., Ogmundsdottir H., and Ingolfsdottir K. Phytomedicine 11 (2004) 602-606
70. Huneck S., and Schreiber K. Phytochemistry 11 (1972) 2429-2434
71. Barros M.T., Maycock C.D., and Ventura M.R. Org. Lett. 5 (2003) 4097-4099
72. For synthesis and applicatons of dimethyl itaconate-anthracene adduct (1):
73. Golfiler M., and Prange T. Bull. Soc. Chim. Fr. (1974) 1159-1160
74. Kodpinid M., Siwapinyoyos T., and Thebtaranonth Y. J. Am. Chem. Soc. 106 (1984) 4862-4865
75. Mahidol C., Thebtaranonth C., Thebtaranonth Y., and Yenjai C. Tetrahedron Lett. 30 (1984) 3857-3860
76. Thebtaranonth Y. Pure Appl. Chem. 69 (1997) 609-614
77. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02, Gaussian: Wallingford, CT, 2004.
78. Dennington, R., II; Keith, T.; Millam, J.; Eppinnett, K.; Hovell, W. L.; Gilliland, R. GaussianView, Version 3.09, Semichem: Shawnee Mission, KS, 2003.
79. Firouzabadi H., and Zeynizadeh F. Bull. Chem. Soc. Jpn. 70 (1997) 155-167 and the references cited therein
80. Hudlicky M. Reduction in Organic Chemistry (1984), Ellis Horwood, Chichester, UK
81. Zeynizadeh B., and Behyar T. Bull. Chem. Soc. Jpn. 78 (2005) 307-315
82. 2O system in reduction, see:
83. Matteoli U., Beghetto V., Schiavon C., Scrivanti A., and Menchi G. Tetrahedron: Asymmetry 8 (1997) 1403-1409
84. Tamami B., and Mahdavi H. Tetrahedron 59 (2003) 821-826
85. Issa F., Fischer J., Turner P., and Coster M.J. J. Org. Chem. 71 (2006) 4703-4705
86. See Ref. 15.