Abstract
This review describes cyclocembrane compounds isolated from plants, marine organisms, and insects. A systematization of cyclized diterpenoids according to the types of carbon skeletons is given.
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Literature cited
J. D. Bu'lock, The Biosynthesis of Natural Products. An Introduction to Secondary Metabolism, McGraw-Hill, London (1965), pp. 57–149.
W. G. Dauben, W. F. Thiessen and P. R. Resnick, J. Am. Chem. Soc.,84, 2015 (1962).
H. Kobayashi and S. Akiyoshi, Bull. Chem. Soc. Jpn.,35, 1044 (1962).
A. J. Weinheimer, C. W. I. Chang, and J. A. Matson, Fortschr. Chem. Org. Naturst,36, 285 (1979).
H. Erdtman, T. Norin, M. Sumimoto, and A. Morrison, Tetrahedron Lett., 3879 (1964).
E. N. Shmidt, N. K. Kashtanova, and V. A. Pentegova, Khim. Prir. Soedin., 694 (1970).
V. A. Raldugin, L. I. Demenkova, and V. A. Pentegova, Khim. Prir. Soedin, 677 (1984).
V. D. Patil, U. R. Nayak and S. Dev, Tetrahedron,29, 341 (1973).
A. J. Blackman, B. F. Bowden, J. C. Coll, B. Frick, M. Mahendran, and S. I. Mitchell, Aust. J. Chem.,35, 1873 (1982).
A. I. Birch, W. V. Brown, I. E. T. Corrie, and B. P. Moore, J. Chem. Soc. Perkin Trans. I, 2653 (1972).
S. Carmely, A. Groweiss, and A. Kashman, J. Org. Chem.,46, 4279 (1981).
B. Karlsson, A.-M. Pilotti, A.-Ch. Söderholm, T. Norin, S. Sundin, and M. Sumimoto, Tetrahedron,34, 2349 (1978).
S. Hasegawa and Y. Hirose, Phytochemistry,24, 2041 (1985).
A. A. Adesomoju, J. I. Okogun, M. P. Cava, and P. J. Carroll, Heterocycles,20, 2125 (1983).
A. A. Adesomoju and J. I. Okogun, J. Nat. Prod.,47, 308 (1984).
B. A. Burke, W. R. Chan, V. A. Honkon, J. F. Blount, and P. S. Manhand, Tetrahedron,36, 3489 (1980).
E. Fujita, K. Fuji, Y. Nagao, and M. Node, Bull. Inst. Chem. Res., Kyoto Univ.,52, 385 (1979).
B. Lythgoe, K. Nakanishi, and S. Uyeo, Proc. Chem. Soc. (London), 301 (1964).
Lukas, Arch. Pharm.,56, 145 (1856).
E. Graf and H. Boeddeker, Arch. Pharm.,289, 364 (1956).
J. M. Baxter, B. Lythgoe, B. Scales, and S. Trippett, Proc. Chem. Soc. (London), 9 (1958).
J. M. Baxter, B. Lythgoe, B. Scales, R. M. Scrowiston, and S. Trippett, J. Chem. Soc., 2964 (1962).
D. H. Eyre, J. M. Harrison, R. M. Scrowston, and B. Lythgoe, Proc. Chem. Soc. (London), 271 (1963).
M. Kurono, Y. Nakadaira, S. Onuma, K. Sasaki, and K. Nakanishi, Tetrahedron Lett., 2153 (1963).
K. Ueda, S. Ueyo, Y. Yamamoto, and Y. Maki, Tetrahedron Lett., 2176 (1963).
B. Lythgoe, K. Nakanishi, and S. Uyeo, Proc. Chem. Soc. (London), 301 (1964).
M. Dukes, D. H. Eyre, J. W. Harrison, and B. Lythgoe, Tetrahedron Lett., 4765 (1965).
M. Kurono, Y. Maki, N. Nakanishi, M. Ohashi, K. Ueda, S. Uyeo, C. M. Woods, and Y. Yamamoto, Tetrahedron Lett., 1917 (1965).
M. Shiro, T. Sato, H. Koyama, Y. Maki, K. Nakanishi, and S. Uyeo, J. Chem. Soc., Chem. Commun., 97 (1966).
M. Duke, D. H. Eyre, J. W. Harrison, R. M. Scrowstone, and B. Lythgoe, J. Chem. Soc. (C), 448 (1967).
W. R. Chan, T. G. Halsall, G. H. Hornby, A. W. Oxford, W. Sabel, K. Bjomer, G. Ferguson, and J. M. Robertson, J. Chem. Soc., Chem. Commun.,923 (1966).
M. Miyazaki, K. Shimizu, H. Mishime, and M. Kuraboyashi, Chem. Pharm. Bull.,16, 546 (1968).
H.-C. Chiang, M. C. Woods, K. Nakanishi, and Y. Nakadaira, J. Chem. Soc., Chem. Commun., 1201 (1967).
M. C. Woods, H.-C. Chiang, Y. Nakadaira, and K. Nakanishi, J. Am. Chem. Soc.,20, 522 (1968).
D. H. Della Casa de Marcano and T. G. Halsall, J. Chem. Soc., Chem. Commun.,21, 1282 (1969).
D. H. Della Casa de Marcano and T. G. Halsall, J. Chem. Soc., Chem. Commun.,21, 1381 (1970).
D. H. Della Casa de Marcano and T. G. Halsall, J. Chem. Soc., Chem. Commun., 1382 (1970).
D. H. Della Casa de Marcano and T. G. Halsall, J. Chem. Soc., Chem. Commun., 365 (1975).
M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, and A. McPhail, J. Am. Chem. Soc.,93, 2325 (1971).
R. W. Miller, R. G. Powell, C. R. Smith, E. Arnold, and J. Clardy, J. Org. Chem.,46, 1469 (1981).
G. Chauviere, D. Guenard, C. Pascard, F. Picot, P. Potier, and T. Pranget, J. Chem. Soc., Chem. Commun., 495 (1982).
R. W. Miller, R. G. Powell and C. R. Smith, US Patent No. 4,206,221 [Chem. Abstr., No. 17, 168465 (1980)].
J. L. McLaughlin, R. W. Miller, R. G. Powell, and C. R. Smith, Jr., J. Nat. Prod.,44, 312 (1981).
C. S. Swindell and S. J. Salms, Tetrahedron,25, 3801 (1984).
N. Harribert, B. Siegfried, S. Walfgang, and J. Martin, Angew. Chem.,96, 303 (1984).
H. Hagaoka, K. Ohsawa, T. Takata, and Y. Yamata, Tetrahedron Lett.,25, 5389 (1984).
M. J. Begley, C. B. Jackson, and G. Pattenden, Tetrahedron Lett.,26, 3397 (1985).
I. Wahlberg, A.-M. Eklung, J. Nishida, and C. R. Enzell, Tetrahedron Lett.,24, 843 (1983).
O. Kennard, D. G. Watson, L. R. di Sanseverino, B. Tursch, R. Bosmans, and C. Djerassi, Tetrahedron Lett.,24, 2879 (1968).
G. Aranda, J. C. Braekman, J. Call, D. Daloze, and B. Tursch, Colloq. Int. CNRS (1980), p. 103.
Y. Uchio, H. Naboya, M. Nakyama, S. Hayashi, and T. Hase, Tetrahedron Lett.,22, 1689 (1981).
R. Kazlauskas, P. T. Murphy, R. J. Wells and P. Schönholzer, Tetrahedron Lett.,52, 4643 (1977).
T. C. Hochlowski and D. J. Faulkner, Tetrahedron Lett.,21, 4055 (1980).
Y. Kashman, Tetrahedron Lett.,21, 879 (1980).
V. A. Raldugin, S. A. Shevtsov, V. I. Mamatyuk, and V. A. Pentegova, Sibirskogo Otd. Akad. Nauk, SSSR, Ser. Khim. Nauk, Issue No. 15, Series No. 1, p. 98 (1986).
D. B. Stierle, B. Carte, D. J. Faulkner, B. Tagle, and J. Clardy, J. Am. Chem. Soc.,102, 5088 (1980).
S. J. Selover, P. Creras, B. Tagle, and J. Clardy, J. Org. Chem.,46, 964 (1981).
J. E. Burks, D. Van der Helm, C. Y. Chonge and L. C. Ciereszko, Acta Crystallogr., Sect. B,B33, 704 (1972).
A. J. Wratten, D. J. Faulkner, K. Hirotsu, and J. Clardy, J. Am. Chem. Soc.,99, 2824 (1977).
S. J. Wratten and D. J. Faulkner, Tetrahedron,35, 1907 (1979).
S. J. Wratten, W. Fenical, D. J. Faulkner, and T. C. Wekell, Tetrahedron Lett.,18, 1559 (1977).
B. N. Ravi, J. F. Marwood, and R. I. Wells, Aust. J. Chem.,33, 2307 (1980).
S. H. Grode, T. R. James, and J. H. Cardellina, Tetrahedron Lett.,24, 691 (1983).
J. Yao, J. Qian, H. Fan, K. Shih, S. Huang, Y. Liin, and K. Long, Zhongshan Daxue Xuebao, Ziran Kexueban, 83 (1984) (Chem. Abstr.,101, 211491c).
A. Clasters, A. Ahond, P. Laboute, C. Poupat, and P. Potier, J. Nat. Prod.,47, 155 (1984).
A. Clasters, P. Laboute, A. Ahond, C. Poupat, and P. Potier, J. Nat. Prod.,47, 162 (1984).
S. A. Look, W. Fenical, D. van Engen, and J. Clardy, J. Am. Chem. Soc.,106, 5026 (1984).
G. H. Prestwich, S. P. Tanis, J. P. Springer, and J. Clardy, J. Am. Chem. Soc.,98, 6061 (1976).
J. C. Braekman, D. Daloze, A. Dupont, J. Pasteels, B. Tursch, J. P. Declerq, G. Germain, and M. van Meerssche, Tetrahedron Lett.,21, 27 (1980).
R. Baker, A. J. Organ, K. Prout, and R. Jones, Tetrahedron Lett.,25, 579 (1984).
G. D. Prestwich, S. P. Tanis, F. G. Pilkiewicz, I. Miura, and K. Nakanishi, J. Am. Chem. Soc.,98, 6062 (1976).
J. Vrkoc, M. Budesinsky, and P. Sedmera, Collect. Czech. Chem. Commun.,43, 1125 (1978).
J. Vrkoc, M. Budesinsky, and P. Sedmera, Collect. Czech. Chem. Commun.,43, 2473 (1978).
G. D. Prestwich, Experientia,34, 682 (1978).
J. C. Braekman, D. Daloze, A. Dupont, J. M. Arrieta, C. Piccini-Leopardi, G. Germain, and M. van Meerssche, Bull Soc. Chim. Belg.,92, 111 (1983).
G. D. Prestwich, S. G. Spanton, and Y. P. Tho, Tetrahedron Lett.,22, 1563 (1981).
A. Dupont, Y. P. Braekman, D. Daloze, J. M. Posdeels and B. Tursch, Bull Soc. Chim. Belg.,90, 485 (1981).
J. C. Braekman, D. Daloze, A. Dupont, J. M. Posteels, and R. Ottinger, Bull. Soc. Chim. Belg.,93, 291 (1984).
G. D. Prestwich, B. A. Solheim, J. Clardy, F. G. Pilkiewicz, J. Miura, S. P. Tanis, and K. Nakanishi, J. Am. Chem. Soc.,99, 8082 (1977).
G. D. Prestwich, S. H. Goh, and Y. P. Tho, Experientia,37, 11 (1981).
G. D. Prestwich, J. W. Louher, and M. S. Collins, Tetrahedron Lett., 3827 (1979).
S. Cerrini, D. Lamba, D. Budesinsky, and I. Valteroa, in: 11th Conference on Isoprenoids. Abstracts of Papers, Jahranka (Poland), September 16–21 (1985), p. 22.
G. D. Prestwich, S. G. Spanton, L. M. Louher, and J. Vrkoc, J. Am. Chem. Soc.,102, 6825 (1980).
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Novosibirsk Institute of Organic Chemistry, Siberian Branch, USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 327–342, May–June, 1987.
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Raldugin, V.A., Shevtsov, S.A. Polycyclic diterpenoids biogenetically related to the cembranoids. Chem Nat Compd 23, 269–281 (1987). https://doi.org/10.1007/BF00600822
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DOI: https://doi.org/10.1007/BF00600822