Synthetic investigations in the field of drimane sesquiterpenoids

Studies in Natural Products Chemistry

Volumn 33, Issue PART M, 2006, Pages 393-432

  Vlad, Pavel F ^a  

^a INSTITUTE OF CHEMISTRY   (Moldova)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77950213037     PISSN: 15725995     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1572-5995(06)80031-1     Document Type: Chapter

References (119)

1. Nomenclature of Organic Compounds (1979), Section D,E, F and H, Pergamon Press, Weinheim
2. Appel H.H., Brooks CJ.W., and Overton K.H. J. Chem. Soc. (1959) 3322-3332
3. Jansen B.J.M., and de Groot A. Nat. Prod. Rep. 8 (1991) 309-318
4. Jansen B.J.M., and de Groot A. Nat. Prod. Rep. 21 Nr. 4 (2004)
5. De Groot A., and van Beek T.A. Rec. Trav. Chim. Pays-Bas 106 (1987) 1-18
6. Jansen B.J.M., and de Groot A. Nat. Prod. Rep. 8 (1991) 319-337
7. Vlad P.F., Koltsa M.N., and Mironov G.N. Russ. Chem. Bull. 46 (1997) 855-873
8. (in Russian). Vlad P.F., and Koltsa M.N. Synthesis and Application of Odorous Compounds from Labdane Diterpenoids, Kishinev, Shtiintsa (1988)
9. Brooks C.J.W., and Draffan G.H. Tetrahedron 25 (1969) 2865-2885
10. Kioy D., Gray A.I., and Waterman P.G. Phytochemistry 29 (1990) 3535-3538
11. Asakawa Y., Toyota M., and Takemoto T. Phytochemistry 17 (1978) 457-460
12. Fukuyama Y., Sato T., Asakawa Y., and Takemoto T. Phytochemistry 21 (1982) 2895-2898
13. Asakawa Y., Toyota M., and Cheminat A. Phytochemistry 25 (1986) 2555-2556
14. Toyota M., Ooiso Y., Kusuyama T., and Asakawa Y. Phytochemistry 35 (1994) 1263-1266
15. Dembitskii A.D., Crotova G.I., and Zamcova V.V. Izv. Acad. Nauk Kaz. SSR ser. khim. No 6 (1991) 63-65
16. Fraga B.M. Natur. Prod. Rep. 12 (1995) 303-321
17. De Bernardi M., Mellerio G., Vidari G., and Vita-Finzi P. J. Chem. Soc., Perkin Trans. 1 (1980) 221-226
18. Cortes M.J., Razmilic I., Sierra J.R., and Lopez J. Chem.Ind. (1985) 735
19. Razmilic J., Lopez J., Sierra J.a., and Cortes M. Synth. Commun. 17 (1987) 95-103
20. Kubo L., Lee Y.W., Pettei M., Pilkiewicz F., and Nakanishi K. J. Chem. Soc., Chem. Commun (1976) 1013-1014
21. Caproli V., Cimino G., Colla R., Gavagnin M., Sodano G., and Spinella A. J. Nat. Prod. 50 (1987) 146-151
22. Paul V.J., Seo Y., Cho K.W., Rho J.R., Shin J., and Bergguist P.R. J. Nat. Prod. 60 (1997) 1116-1120
23. Banthorpe D.V., Brooks C.J.W., Brown J.T., Leppin G.J., and Morris G.S. Phytochemistry 2S (1989) 1631-1633
24. Asakawa Y., and Takemoto T. Experientia 35 (1979) 1420-1521
25. Hemejima M., and Kubo L. J. Nat. Prod. 35 (1992) 620-625
26. Oyarzum M.L., Cortes M., and Sierra J. Synth. Commun. 12 (1982) 951-958
27. Urones J.G., Marcos I.S., Gomez-Perez B., Diez D., Lithgow A.M., Gomez P.M., Basabe P., and Garrido N.M. Tetrahedron 50 (1994) 10995-11012
28. Cortes M., Razmilic I., and Lopez J. J. Nat. Prod. 53 (1990) 1369-1371
29. Canonica L., Corbella A., Gariboldi P., Jommi G., Krepinsky J., Ferrari G., and Casagrande C. Tetrahedron 25 (1969) 3895-3902
30. Brooks C.J.W., and Draffan G.H. Tetrahedron 25 (1969) 2887-2898
31. Lopez J., Sierra J., and Cortes M. Chem. Lett. (1986) 2073-2074
32. De Bernardi M., Mellerio G., Vidari G., and Vita-Finzi P. J. Chem. Soc., Perkin Trans. 1 (1983) 2739-2743
33. Aasen A.J., Vogt C.H.G., and Enzell C.R. Acta Chem. Scand. B29 (1975) 51-55
34. Aasen A.J., and Enzell C.R. Acta Chem. Scand. B28 (1975) 1239-1240
35. Schumacher J.N., and Vesta L. Tobacco Sci. 18 (1974) 43-48
36. Hlubucek J.R., Aasen A.J., Kimland B., and Enzell C.R. Phytochemistry 12 (1973) 2555-2557
37. Cuellar M.A., Moreno L.E., and Preite M.D. Arkivoc (2003) 169-177
38. Cortes M., Lopez J., and Diaz E. Nat. Prod. Lett. 2 (1993) 37-40
39. Fukuyama Y., Sato T., Miura I., and Asakawa Y. Phytochemistry 24 (1985) 1521-1524
40. Gonzalez-Sierra M., de los Angeles Laborde M., and Ruveda E.A. Synth. Commun. 17 (1987) 431-441
41. Wenkert E., and Strike D.P. J. Am. Chem. Soc. 86 (1964) 2044-2050
42. Pelletier S.W., Lajsic S., Ohtsuka Y., and Djarmati Z. J. Org. Chem. 40 (1975) 1607-1609
43. Akita H., Nozawa M., Mitsuda A., and Ohsawa H. Tetrahedron Asymmetry 11 (2000) 1375-1388
44. Hueso-Rodriguez J.A., Dominguez G., and Rodriguez B. An. Quim., ser C 84 (1988) 215-218
45. Barrero A.F., Manzaneda E.A., Altarejos J., Salido S., and Ramos J.M. Tetrahedron Lett. 35 (1994) 2945-2948
46. Barrero A.F., Manzaneda E.A., Altarejos J., Salido S., Ramos J.M., Simmonds M.S.J., and Blaney W.M. Tetrahedron 51 (1995) 7435-7450
47. Lagnel B.M.F., Morin C., and de Groot A. Synthesis (2000) 1907-1916
48. Vlad P.F., Kryshtal G.V., and Lazurievskii G.V. Zh. Obshch. Khim. 37 (1967) 2187-2190
49. [45] Schumacher J.N., Henley W.M. and Teague C.E.; US Patent 3050532.
50. Kuchkova K.I., Chumakov Y.M., Simonov Y.A., Bocelli G., Panasenco A.A., and Vlad P.F. Synthesis (1997) 1045-1048
51. Ariku A.N., Koltsa M.N., Vlad P.F., Kukovinets O.S., Odinokov V.N., and Tolstikov G.A. Khim. Prirod. Soedin, (Chem. Nat. Comp.) (1991) 343-349
52. Odinokov V.N., Vlad P.F., Kukovinets O.S., Isakova L.A., Lindeman S.V., Struchkov Yu.T., and Tolstikov G.A. Dokl. Akad Nauk SSSR 269 (1983) 853-855
53. Vlad P., Cucicova C., and Aricu A. Patent of the Republic of Moldova (2002) 2018
54. Vlad P.F., Ungur N.D., and Perutsky V.B. Khim. Prirod. Soedin (Chem. Nat. Comp.) 793 (1986)
55. Vlad P.F. Pure Appl. Chem. 65 (1993) 1329-1336
56. Polovinca M.P., Korchagina D.V., Gatilov Y.G., Bagrianskaya I.Y., Barkhash V.A., Shcherbukhin V.V., Zefirov N.S., Perutskii V.B., Ungur N.D., and Vlad P.F. J. Org. Chem. 59 (1994) 1509-1517
57. Vlad P.F., Ungur N.D., Hung N.V., and Perutsky V.B. Russ. Chem. Bull. (Engl. Transl) 44 (1995) 2390-2403
58. Hlubucek J.R., Aasen A.J., Kimland B., and Enzell C.R. Acta Chem. Scand. B28 (1974) 289-294
59. Goodwin T.F., Rasmussen E.L., Guinn A.C., Me K.S.S., Gunawardena R., Riddle S.W., and Riddle H.S. J. Nat. Prod. 62 (1999) 1570-1572
60. Ohloff G., and Giersch W. Croat Chun. Acta 58 (1985) 491-509
61. Hlubucek J.R., Aasen A.J., Almqvist S.O., and Enzell C.R. Acta Chem. Scand. B28 (1974) 18-22
62. Poigny S., Huor T., Guyot M., and Samadi M. J. Org. Chem. 64 (1999) 9318-9320
63. Hellou J., Andersen R.J., and Thomson J.E. Tetrahedron 38 (1982) 1875-1879
64. Shishido K., Tokunaga Y., Omachi N., Hiroya K., Fukumoto K., and Kametani T. J. Chem. Soc., Perkin Trans. 1 (1990) 2481-2486
65. Ohta Y., Andersen N.H., and Liu C.B. Tetrahedron 33 (1977) 617-628
66. Wada K., Tanaka S., and Marumo S. Agric. Biol. Chem. 47 (1993) 1075-1078
67. Shishido K., Omodani T., and Shibuya M. J. Chem. Soc., Perkin Trans. 1 (1991) 2285-2287
68. Ruzicka L., Seidel C.F., and Engel L.L. Helv. Chim. Acta. 25 (1942) 621-630
69. Aricu A.N., Andreeva I.Yu., and Vlad P.F. Russ. Chem. Bull. (Engl. Transl.) 45 (1996) 2644-2648
70. Aricu A.N., and Vlad P.F. Khim. Prirod. Soedin (Chem. Nat. Comp.) (2000) 124-125
71. Barton D.H.R., Taylor D.K., and Tse C. Tetrahedron Lett. 51 (1994) 9505-9508
72. Coltsa M.N., Mironov G.N., Aricu A.N., and Vlad P.F. Khim. Prirod. Soedin, (Chem. Nat. Comp.) (1991) 45-50
73. Chircova M.A., and Pentegova V.A. Khim. Prirod. Soedin, (Chem. Nat. Comp.) (1969) 247-251
74. Vlad P.F., Coltsa M.N., and Russo A.G. Zh. Obshch. Khim. (J. Gen. Chem.) 43 (1973) 650-655
75. Leite M.A.F., Sarragiotto M.H., Imamura P.M., and Marsaioli A.J. J. Org. Chem. 57 (1986) 5409-5410
76. Hueso-Rodriguez J.A., and Rodriguez B. Tetrahedron 45 (1989) 1567-1576
77. Vlad P.F., Aricu A.N., and Ciocirlan A.G. Russ. Chem. Bull. Int. Ed. 53 (2004) 453-455
78. Ohloff G. Helv. Chim. Acta 41 (1958) 845-850
79. Lithgow A.M., Marcos I.S., Basabe P., Sexmero J., Diez D., Gomez A., Estrella A., and Urones J.G. Natur. Prod. Lett. 6 (1995) 291-294
80. Banerjee A.K., Correa J.A., and Laya-Mino M. J. Chem. Soc. Synop. (1998) 710-711
81. Vlad P.F., Coltsa M.N., Sibirtseva V.E., and Kustova S.D. Zh. Obshch. Khim. (J. Gen. Chem. USSR) 50 (1980) 213-217
82. [75] Vlad P.F., Belfer A.G., Coltsa M.N. and Sibirtseva V.E., USSR Patent 777055 (1980).
83. Iastrebova A., Panfil G., Rotundu F., Cojocaru D., Diaconu G., Ciubara M., Vlad P., Coltsa M., Mironov G., Ceban P., Botsan V., and Muntean G. Patent of the Republic of Moldova 235 (1995)
84. USSR Patent 767083 (1980). Vlad P.F., and Vorobieva E.A. Khim. Prirod. Soedin. (Chem. Nat. Compd.) (1983) 146-149
85. Stoll M., and Hinder M. Helv. Chim. Acta 37 (1954) 1859-1865
86. Koltsa M.N., Mironov G.N., Malinovskii S.T., and Vlad P.F. Russ. Chem. Bull. (Engl Transl) 45 (1996) 208-214
87. Razmilic I., Lopez J., and Cortes M. Synth. Commun. 23 (1993) 1155-1173
88. Barrero A.F., Cortes M., Manzanenda E.A., Cabrera E., Chahboun R., Lara M., and Rivas A.R. J. Nat. Prod. 62 (1999) 1488-1491
89. Vlad P.F., Popa D.P., Gorincioi E.C., Coltsa M.N., and Mironov G.N. Russ. Chem. Bull. Int. Ed. 49 (2000) 98-101
90. Chumakov Yu.M., Simonov Yu.A., Mazus M.D., Popa D.P., and Vlad P.F. Crystallography Reports (Engl. Transl.) 45 (2000) 244-247
91. Nakata T., Akita H., Naito T., and Oishi T. Chem. Pharm. Bull. 28 (1980) 2172-2177
92. Nacano T., Villamizar J.E., and Maillo M.A. Tetrahedron 55 (1999) 1561-1568
93. Nacano T., and Maillo M.A. Synth. Commun. 11 (1981) 463-473
94. Nacano T., and Martin A. J. Chem Research (S) (1989) 52-53
95. Kravtsov V.N., Gorincioi E.C., Mironov G.N., Coltsa M.N., Simonov Yu.A., and Vlad P.F. Crystallography Reports (Engl. Transl.) 45 (2000) 289-291
96. Appel H.H., Bond R.P.M., and Overton K.H. Tetrahedron 19 (1963) 635-641
97. Harrijan G.G., Ahmad A., Baj N., Glass T.E., Gunatilaka A.A.L., and Kingston D.G.I. J. Nat. Prod. 56 (1993) 921-925
98. Appel H.H., Connolly J.D., Overton K.H., and Bond R.P.M. J. Chem. Soc. (1960) 4685-4692
99. Vlad P.F., Gorincioi E.C., Coltsa M.N., and Deleanu C. Russ. Chem. Bull. Int. Ed. 49 (2000) 546-548
100. Kravtsov V.N., Simonov Yu.A., Gorincioi E.C., Coltsa M.N., and Vlad P.F. Crystallography Reports (Engl Transl.) 45 (2000) 789-791
101. Razmilic I., Sierra J., Lopez J., and Cortes M. Chem. Lett. (1985) 1113-1114
102. Gorincioi E., Popa D., Mironov G., Coltsa M., and Vlad P. Abstracts of XXVI National Sympozium on Chemistry, Calimanesti-Caciulata. Vâlcea, Roumania (2000) 141
103. Kaneko H., and Hoshino K. Agric. Biol. Chem. 33 (1969) 969-970
104. Schumacher J.N., and Heckman R.A. Phytochemistryt 10 (1971) 421-423
105. Hoye T.R., and Kurth M.J. J. Org. Chem. 43 (1978) 3693-3697
106. Strekowski L., Visnick M., and Battiste M.A. J. Org Chem. 51 (1986) 4836-4839
107. Mori K., and Nacazono Y. Tetrahedron 42 (1986) 283-290
108. Bricout J., Viani R., Muggler-Chavan F., Marion J.P., Reymond D., and Egli R.H. Helv Chim. Ada. 50 (1967) 1517-1522
109. Ina K., Sacato Y., and Fukami H. Tetrahedron Lett. (1968) 2777-2780
110. Kaneko H., and Ijichi K. Agric. Biol. Chem. 32 (1968) 1337-1340
111. Viani R., Bricout J., Marion J.P., Muggler-Chavan F., Reymond D., and Egli R.H. Helv Chim. Ada. 52 (1969) 887-891
112. Sacan T., Isoe S., and Hueon S.B. Tetrahedron Lett. (1967) 1263-1627
113. Demole E., Enggist P., and Stoll M. Helv Chim. Ada. 52 (1969) 24-32
114. [104] Schumacher J.N.; US Patent 3.576.008.
115. Vlad P.F., Gorincioi E.C., Aricu A.N., and Coltsa M.N. Nat. Prod. Lett. 13 (1999) 1-4
116. Hashimoto S., Sonegawa M., Sakata S., and Ikegami S. J. Chem. Soc., Chem. Commun. (1987) 24-25
117. Gabetta B., Zini G., and Danieli B. Phytochemistry 28 (1989) 859-862
118. Coltsa M.N., Mironov G.N., and Vlad P.F. Khim. Prirod. Soedin. (Chem. Nat. Comp.) (1991) 214-220
119. Coltsa M.N., Mironov G.N., and Vlad P.F. Khim. Prirod. Soedin. (Chem. Nat. Comp.) (1991) 499-502