The structural chemistry, reactivity, and total synthesis of dolabellane diterpenes

Tetrahedron

Volumn 54, Issue 39, 1998, Pages 11683-11729

  Rodríguez, Abimael D ^{a,b,c,d,e,f,g,h}   González, Eduvigis ^a,h,i,j   Ramírez, Catherine ^a,h,k  

^a UNIVERSITY OF PUERTO RICO RIO PIEDRAS   (Puerto Rico)

^b UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^c JOHNS HOPKINS UNIVERSITY   (United States)

^d NATIONAL INSTITUTES OF HEALTH   (United States)

^e MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^f MIT

^g UNIVERSITY OF HAWAII   (United States)

^h UNIVERSITY OF PUERTO RICO   (Puerto Rico)

ⁱ Margarita Janer Palacios High School   (Puerto Rico)

^j Marine Natural Products Chemistry

^k Stella Márquez High School   (Puerto Rico)

more..

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; DOLABELLANE; NATURAL PRODUCT; PLANT EXTRACT; UNCLASSIFIED DRUG;

ALGA; ALKYLATION; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; COELENTERATE; CYCLIZATION; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGUS; ISOLATION PROCEDURE; MOLLUSC; MOSS; NONHUMAN; PRIORITY JOURNAL; REVIEW; STRUCTURE ANALYSIS;

ALGAE; BRYOPHYTA; COELENTERATA; FUNGI; MOLLUSCA;

EID: 0032563996     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)83033-0     Document Type: Review

References (85)

1. Compiled from data in recent reviews; see Faulkner DJ. Nat. Prod. Rep. 1997; 14: 259-302 and previous papers in this series.
2. Borschberg H-J. Zur Biogenese des Sordarins. Eidgenøssischen Technischen Hochschule, Zürich, 1975.
3. Jenny L, Borschberg H-J. Helv. Chim. Acta 1995; 78: 715-731.
4. Ireland C, Faulkner DJ, Finer J, Clardy J. J. Am. Chem. Soc. 1976; 98: 4664-4665.
5. Ireland C, Faulkner DJ. J. Org. Chem. 1977; 42: 3157-3162.
6. González AG, Martín JD, Norte M, Pérez R, Weyler V, Rafii S, Clardy J. Tetrahedron Lett. 1983; 24: 1075-1076.
7. González AG, Cataldo F, Fernández J, Norte M. J. Nat. Prod. 1987; 50: 1158-1159.
8. Bowden BF, Coll JC, Mitchell SJ, Stokie GJ, Blount JF. Aust. Chem. 1978; 31: 2039-2047.
9. Bowden BF, Braekman J-C, Coll JC, Mitchell SJ. Aust J. Chem. 1980; 33: 927-932.
10. Horeau A, Nouaille A. Tetrahedron Lett. 1971; 1939-1942.
11. Kobayashi M, Son BW, Kyogoku Y, Kitagawa I. Chem. Pharm. Bull. 1986; 34: 2306-2309.
12. Bowden BF, Coll JC, Gulbis JM, Mackay MF, Willis RH. Aust. J. Chem. 1986; 39: 803-812.
13. Subrahmanyam C, Rao CV, Anjaneyulu V, Satyanarayana P, Rao PVS, Ward RS, Pelter A. Tetrahedron 1992; 48: 3111-3120.
14. Kobayashi M, Son BW, Fujiwara T, Kyogoku Y, Kitagawa I. Tetrahedron Lett. 1984; 25: 5543-5546.
15. Nakanishi K, Dillon J. J. Am. Chem. Soc. 1971; 93: 4058-4060.
16. Mon K, Iguchi K, Yamada N, Yamada Y, Inouye Y. Tetrahedron Lett. 1987; 28: 5673-5676.
17. Mori K, Iguchi K, Yamada N, Yamada Y, Inouye Y. Tennen Yuki Kagobutsu Toronkai 1987; 29: 287-294.
18. Mori K, Iguchi K, Yamada N, Yamada Y, Inouye Y. Chem. Pharm. Bull. 1988; 36: 2840-2852.
19. Look SA, Fenical W. J. Org. Chem. 1982; 47: 4129-4134.
20. Su J, Zhong Y, Shi K, Cheng Q, Snyder JK, Hu S, Huang Y. J. Org. Chem. 1991; 56: 2337-2344.
21. Su J, Zhong Y, Zeng L. J. Nat. Prod. 1991; 54: 380-385.
22. Su J-Y, Zhong Y-L, Zeng L-M. Chin. J. Chem. 1992; 10: 155-160.
23. Li J-C, Zhang Z-M, Xia Z-X, Ni C-Z, Wu Y-L. Acta Chim. Sin. 1987; 45: 558-563.
24. Xia Z, Zhang Z, Huang J. Jie Gou Hua Xue 1986; 5: 263-266.
25. Sullivan GR, Dale JA, Mosher HS. J. Org. Chem. 1973; 38: 2143-2147.
26. Corey EJ, Kania RS. J. Am. Chem. Soc. 1996; 118: 1229-1230.
27. Shin J, Fenical W. J. Org. Chem. 1991; 56: 3392-3398.
28. Cáceres J, Rivera ME, Rodríguez AD. Tetrahedron 1990; 46: 341-348.
29. Rodríguez AD, Acosta AL, Dhasmana H. J. Nat. Prod. 1993; 56: 1843-1849.
30. Rodríguez AD, González E, González C. J. Nat. Prod. 1995; 58: 226-232.
31. Govindan M, Govindan GN, Kingston DGI. J. Nat. Prod. 1995; 58: 1174-1184.
32. Sun HH, Fenical W. Phytochemistry 1979; 18: 340-341.
33. Amico V, Oriente G, Piattelli M, Tringali C, Fattorusso E, Magno S, Mayol L. Tetrahedron 1980; 36: 1409-1414.
34. Piattelli M, Tringali C, Neri P, Rocco C. J. Nat. Prod. 1995; 58: 697-704.
35. Tringali C, Piattelli M, Nicolosi G. Tetrahedron 1984; 40: 799-803.
36. Tringali C, Oriente G, Piattelli M, Nicolosi G. J. Nat. Prod. 1984; 47: 615-619.
37. Amico V, Currenti R, Oriente G, Piattelli M, Tringali C. Phytochemistry 1981; 20: 848-849.
38. Tringali C, Nicolosi G, Piattelli M, Rocco C. Phytochemistry 1984; 23: 1681-1684.
39. Tringali C, Oriente G, Piattelli M, Nicolosi G. J. Nat. Prod. 1985; 48: 484-485.
40. Harada N, Iwabuchi J, Yokota Y, Uda H, Nakanishi K. J. Am. Chem. Soc. 1981; 103: 5590-5591.
41. Gonnella NC, Nakanishi K, Martin WS, Sharpless KB. J. Am. Chem. Soc. 1982; 104: 3775-3776.
42. Rao CB, Pullaiah KC, Surapaneni RK, Sullivan BW, Albizati KF, Faulkner DJ, He C-H, Clardy J. J. Org. Chem. 1986; 51: 2736-2742.
43. Konig GM, Wright AD, Fronczek FR. J. Nat. Prod. 1994; 57: 1529-1538.
44. Konig GM, Wright AD. Tetrahedron 1994; 50: 8011-8018.
45. Durán R, Zubía E, Ortega MJ, Salvá J. Tetrahedron 1997; 53: 8675-8688.
46. Wright AD, Coll JC, Price IR. J. Nat Prod. 1990; 53: 845-861.
47. Wright AD, Konig GM, Sticher O. Tetrahedron 1990; 46: 3851-3858.
48. Wright AD, Konig GM, Sticher O, Lubini P, Hofmann P, Dobler M. Helv. Chim. Acta 1991; 74: 1801-1807.
49. Konig GM, Wright AD, Sticher O, Angerhofer CK, Pezzuto JM. Planta Med. 1994; 60: 532-537.
50. Rao CB, Trimurtulu G, Rao DV, Bobzin SC, Kushlan DM, Faulkner DJ. Phytochemistry 1991; 30: 1971-1976.
51. Matsuo A, Uohama K, Hayashi S, Connolly JD. Chem. Lett. 1984; 599-602.
52. Konig GM, Wright AD, Sticher O. Phytochemistry 1991; 30: 3679-3682.
53. Rao CB, Trimurtulu G, Sreedhara C, Rao DV, Bobzin SC, Faulkner DJ. Phytochemistry 1994; 37: 509-513.
54. De Rosa S, De Stefano S, Macura S, Trivellone E, Zavodnik N. Tetrahedron 1984; 40: 4991-4995.
55. Van Onckelen HA, Verbeek R. Phytochemistry 1972; 11: 1677-1680.
56. Goez CE, Wright AD, Konig GM, Sticher O. Phytochem. Anal. 1994; 5: 68-73.
57. Matsuo A, Yoshida K, Uohama K, Hayashi S, Connolly JD, Sim GA. Chem. Lett. 1985; 935-938.
58. Matsuo A, Yoshida K, Fukazawa Y, Nakayama M, Kuriyama K. Chem. Lett. 1987; 369-372.
59. Connolly JD, Sim GA, Matsuo A. Acta Cryst 1987; C43: 1422-1424.
60. Matsuo A, Kamio K, Uohama K, Yoshida K, Connolly JD, Sim GA. Phytochemistry 1988; 27: 1153-1159.
61. Hashimoto T, Toyota M, Koyama H, Kikkawa A, Yoshida M, Tanaka M, Takaoka S, Asakawa Y. Tetrahedron Lett. 1998; 39: 579-582.
62. Huneck S, Baxter GA, Cameron AF, Connolly JD, Harrison LJ, Phillips WR, Rycroft DS, Sim GA. J. Chem. Soc., Perkin Trans. 1986; 1: 809-814.
63. Asakawa Y, Lin X, Tori M, Kondo K. Phytochemistry 1990; 29: 2597-2603.
64. Mohamed KM, Ohtani K, Kasai R, Yamasaki K. Phytochemistry 1994; 37: 495-500.
65. Mohamed KM, Ohtani K, Kasai R, Yamasaki K. Phytochemistry 1995; 39: 151-161.
66. Xia Z, Zhang Z. Jie Gou Hua Xue 1984; 3: 29-32.
67. Matsuo A, Yoshida K, Nakayama M. J. Chem. Research (S) 1990; 22-23.
68. Williams DR, Coleman PJ, Henry SS. J. Am. Chem. Soc. 1993; 115: 11654-11655.
69. Williams DR, Coleman PJ. Tetrahedron Lett. 1995; 36: 39-42.
70. Jenny L, Borschberg H-J, Acklin P. Tetrahedron 1996; 52: 1549-1556.
71. Williams DR. Indiana University, Bloomington, personal communication, 1998.
72. Zapp J, Burkhardt G, Becker H. Phytochemistry 1994; 37: 787-793.
73. Mehta G. Pure & Appl. Chem. 1990; 62: 1263-1268.
74. Mehta G, Krishnamurthy N, Karra SR. J. Am. Chem. Soc. 1991; 113: 5765-5775.
75. Mehta G, Karra SR, Krishnamurthy N. Tetrahedron Lett. 1994; 35: 2761-2762.
76. Williams DR, Coleman PJ, Nevill CR, Robinson LA. Tetrahedron Lett. 1993; 34: 7895-7898.
77. Williams DR, Coleman PJ. Tetrahedron Lett. 1995; 36: 35-38.
78. Kato N, Higo A, Nakanishi K, Wu X, Takeshita H. Chem. Lett. 1994; 1967-1970.
79. Corey EJ, Kania RS. Tetrahedron Lett. 1998; 39: 741-744.
80. Luker T, Whitby RJ. Tetrahedron Lett. 1996; 37: 7661-7664.
81. Rodríguez AD, González E, Huang SD. Acta Cryst 1997; C53: 311-313.
82. Ciereszko LS, Karns TKB. Comparative Biochemistry of Coral Reef Coelenterates. In: Jones OA, Endean R, editors. Biology and Geology of Coral Reef. New York: Academic Press, 1973: pp 183-203.
83. Ohta Y, Andersen NH, Liu C-B. Tetrahedron 1977; 33: 617-628.
84. Kato N, Higo A, Wu X, Takeshita H. Heterocycles 1997; 46: 123-127.
85. Huneck S, Overton KH. Phytochemistry 1971; 10: 3279-3281.