Synthesis of spiro-cyclics via ring-closing metathesis

Arkivoc

Volumn 2003, Issue 3, 2003, Pages 67-76

  Kotha, Sambasivarao ^a   Manivannan, Ethirajan ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Allylation; Indane derivatives; Metathesis; Spirocycles

Indexed keywords

1,3 CYCLOPENTANEDIONE; 1,3 DIKETONE DERIVATIVE; 1,3 INDANEDIONE; 2,2 DIALLYL 5,5 DIMETHYLCYCLOHEXANE 1,3 DIONE; 2,2 DIALLYLCYCLOHEXANE 1,3 DIONE; 2,2 DIALLYLINDANE 1,3 DIONE; 5,5 DIMETHYL 1,3 CYCLOHEXANEDIONE; 9,9 DIALLYFLUORENE; DIHYDRORESORCINOL; FLUORENE; KETONE DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; RING CLOSING METATHESIS; SYNTHESIS;

EID: 3042785743     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (49)

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33. For selected reviews on olefin metathesis reaction see: Kotha, S.; Sreenivasachary, N. Indian J. Chem., 2001, 763; Hoyeda, A. M.; Schock, R. R. Chem. Eur. J. 2001, 945; Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; Maier, M. E. Angew. Chem. Int. Ed. Engl. 2000, 39, 2073; Roy, R.; Das, S. K. J. Chem. Soc. Chem. Commun., 2000, 503.
34. For selected reviews on olefin metathesis reaction see: Kotha, S.; Sreenivasachary, N. Indian J. Chem., 2001, 763; Hoyeda, A. M.; Schock, R. R. Chem. Eur. J. 2001, 945; Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18; Maier, M. E. Angew. Chem. Int. Ed. Engl. 2000, 39, 2073; Roy, R.; Das, S. K. J. Chem. Soc. Chem. Commun., 2000, 503.
35. For selected examples of spiro-cyclics by metathesis reaction see: Limieux, R. M.; Devine, P. N.; Mechelke, M. F.; Meyers, A. I.; J. Org. Chem. 1999, 64, 3585; Hammer, K.; Undheim, K. Tetrahedron, 1997, 53, 2309; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247; Bassindale, M. J.; Edwards, A. S.; Hamely, P.; Adams, H.; Harrity, J. P. J. Chem. Soc. Chem. Commun. 2000, 1035; Maity, B. C.; Swamy, V. M.; Sarkar, A. Tetrahedron Lett. 2001, 42 4373.; Gurjar, M. K.; Ravindranath, S. V.; Karmakar, S. Chem. Commun. 2001, 241.; Srikrishna, A.; Srinivasa Rao, M.; Gharpure, S. J.; Chandrasekhar Babu, N. Synlett 2001, 1986; Sabita, G.; Srinivas Reddy, Ch.; Satheesh Babu, R.; Yadav, J. S. Synlett 2001, 1787.
36. For selected examples of spiro-cyclics by metathesis reaction see: Limieux, R. M.; Devine, P. N.; Mechelke, M. F.; Meyers, A. I.; J. Org. Chem. 1999, 64, 3585; Hammer, K.; Undheim, K. Tetrahedron, 1997, 53, 2309; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247; Bassindale, M. J.; Edwards, A. S.; Hamely, P.; Adams, H.; Harrity, J. P. J. Chem. Soc. Chem. Commun. 2000, 1035; Maity, B. C.; Swamy, V. M.; Sarkar, A. Tetrahedron Lett. 2001, 42 4373.; Gurjar, M. K.; Ravindranath, S. V.; Karmakar, S. Chem. Commun. 2001, 241.; Srikrishna, A.; Srinivasa Rao, M.; Gharpure, S. J.; Chandrasekhar Babu, N. Synlett 2001, 1986; Sabita, G.; Srinivas Reddy, Ch.; Satheesh Babu, R.; Yadav, J. S. Synlett 2001, 1787.
37. For selected examples of spiro-cyclics by metathesis reaction see: Limieux, R. M.; Devine, P. N.; Mechelke, M. F.; Meyers, A. I.; J. Org. Chem. 1999, 64, 3585; Hammer, K.; Undheim, K. Tetrahedron, 1997, 53, 2309; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247; Bassindale, M. J.; Edwards, A. S.; Hamely, P.; Adams, H.; Harrity, J. P. J. Chem. Soc. Chem. Commun. 2000, 1035; Maity, B. C.; Swamy, V. M.; Sarkar, A. Tetrahedron Lett. 2001, 42 4373.; Gurjar, M. K.; Ravindranath, S. V.; Karmakar, S. Chem. Commun. 2001, 241.; Srikrishna, A.; Srinivasa Rao, M.; Gharpure, S. J.; Chandrasekhar Babu, N. Synlett 2001, 1986; Sabita, G.; Srinivas Reddy, Ch.; Satheesh Babu, R.; Yadav, J. S. Synlett 2001, 1787.
38. For selected examples of spiro-cyclics by metathesis reaction see: Limieux, R. M.; Devine, P. N.; Mechelke, M. F.; Meyers, A. I.; J. Org. Chem. 1999, 64, 3585; Hammer, K.; Undheim, K. Tetrahedron, 1997, 53, 2309; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247; Bassindale, M. J.; Edwards, A. S.; Hamely, P.; Adams, H.; Harrity, J. P. J. Chem. Soc. Chem. Commun. 2000, 1035; Maity, B. C.; Swamy, V. M.; Sarkar, A. Tetrahedron Lett. 2001, 42 4373.; Gurjar, M. K.; Ravindranath, S. V.; Karmakar, S. Chem. Commun. 2001, 241.; Srikrishna, A.; Srinivasa Rao, M.; Gharpure, S. J.; Chandrasekhar Babu, N. Synlett 2001, 1986; Sabita, G.; Srinivas Reddy, Ch.; Satheesh Babu, R.; Yadav, J. S. Synlett 2001, 1787.
39. For selected examples of spiro-cyclics by metathesis reaction see: Limieux, R. M.; Devine, P. N.; Mechelke, M. F.; Meyers, A. I.; J. Org. Chem. 1999, 64, 3585; Hammer, K.; Undheim, K. Tetrahedron, 1997, 53, 2309; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247; Bassindale, M. J.; Edwards, A. S.; Hamely, P.; Adams, H.; Harrity, J. P. J. Chem. Soc. Chem. Commun. 2000, 1035; Maity, B. C.; Swamy, V. M.; Sarkar, A. Tetrahedron Lett. 2001, 42 4373.; Gurjar, M. K.; Ravindranath, S. V.; Karmakar, S. Chem. Commun. 2001, 241.; Srikrishna, A.; Srinivasa Rao, M.; Gharpure, S. J.; Chandrasekhar Babu, N. Synlett 2001, 1986; Sabita, G.; Srinivas Reddy, Ch.; Satheesh Babu, R.; Yadav, J. S. Synlett 2001, 1787.
40. For selected examples of spiro-cyclics by metathesis reaction see: Limieux, R. M.; Devine, P. N.; Mechelke, M. F.; Meyers, A. I.; J. Org. Chem. 1999, 64, 3585; Hammer, K.; Undheim, K. Tetrahedron, 1997, 53, 2309; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247; Bassindale, M. J.; Edwards, A. S.; Hamely, P.; Adams, H.; Harrity, J. P. J. Chem. Soc. Chem. Commun. 2000, 1035; Maity, B. C.; Swamy, V. M.; Sarkar, A. Tetrahedron Lett. 2001, 42 4373.; Gurjar, M. K.; Ravindranath, S. V.; Karmakar, S. Chem. Commun. 2001, 241.; Srikrishna, A.; Srinivasa Rao, M.; Gharpure, S. J.; Chandrasekhar Babu, N. Synlett 2001, 1986; Sabita, G.; Srinivas Reddy, Ch.; Satheesh Babu, R.; Yadav, J. S. Synlett 2001, 1787.
41. For selected examples of spiro-cyclics by metathesis reaction see: Limieux, R. M.; Devine, P. N.; Mechelke, M. F.; Meyers, A. I.; J. Org. Chem. 1999, 64, 3585; Hammer, K.; Undheim, K. Tetrahedron, 1997, 53, 2309; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247; Bassindale, M. J.; Edwards, A. S.; Hamely, P.; Adams, H.; Harrity, J. P. J. Chem. Soc. Chem. Commun. 2000, 1035; Maity, B. C.; Swamy, V. M.; Sarkar, A. Tetrahedron Lett. 2001, 42 4373.; Gurjar, M. K.; Ravindranath, S. V.; Karmakar, S. Chem. Commun. 2001, 241.; Srikrishna, A.; Srinivasa Rao, M.; Gharpure, S. J.; Chandrasekhar Babu, N. Synlett 2001, 1986; Sabita, G.; Srinivas Reddy, Ch.; Satheesh Babu, R.; Yadav, J. S. Synlett 2001, 1787.
42. For selected examples of spiro-cyclics by metathesis reaction see: Limieux, R. M.; Devine, P. N.; Mechelke, M. F.; Meyers, A. I.; J. Org. Chem. 1999, 64, 3585; Hammer, K.; Undheim, K. Tetrahedron, 1997, 53, 2309; Bassindale, M. J.; Hamley, P.; Leitner, A.; Harrity, J. P. A. Tetrahedron Lett. 1999, 40, 3247; Bassindale, M. J.; Edwards, A. S.; Hamely, P.; Adams, H.; Harrity, J. P. J. Chem. Soc. Chem. Commun. 2000, 1035; Maity, B. C.; Swamy, V. M.; Sarkar, A. Tetrahedron Lett. 2001, 42 4373.; Gurjar, M. K.; Ravindranath, S. V.; Karmakar, S. Chem. Commun. 2001, 241.; Srikrishna, A.; Srinivasa Rao, M.; Gharpure, S. J.; Chandrasekhar Babu, N. Synlett 2001, 1986; Sabita, G.; Srinivas Reddy, Ch.; Satheesh Babu, R.; Yadav, J. S. Synlett 2001, 1787.
43. For details of our earlier work dealing with olefin metathesis reaction see: Kotha, S.; Sreenivasachary, N.; Mohanraja, K.; Durani, S. Bioorg Med. Chem. Lett. 2001, 11, 1421; Kotha, S.; Sreenivasachary, N.; Brahmachary, E. Eur. J. Org. Chem. 2001, 787; Kotha, S.; Sreenivasachary, N. Eur. J. Org. Chem. 2001, 3375; Kotha, S.; Sreenivasachary, N. J. Chem. Soc. Chem. Commun. 2000, 503; Kotha, S.; Halder, S.; Brahmachary, E.; Ganesh, T. Synlett 2000, 853; Kotha, S.; Sreenivasachary, N. Bioorg. Med. Chem. Lett. 1998, 8, 257; Kotha, S.; Sreenivasachary, N.; Brahmachary, E.; Tetrahedron Lett. 1998, 39, 2805.
44. For details of our earlier work dealing with olefin metathesis reaction see: Kotha, S.; Sreenivasachary, N.; Mohanraja, K.; Durani, S. Bioorg Med. Chem. Lett. 2001, 11, 1421; Kotha, S.; Sreenivasachary, N.; Brahmachary, E. Eur. J. Org. Chem. 2001, 787; Kotha, S.; Sreenivasachary, N. Eur. J. Org. Chem. 2001, 3375; Kotha, S.; Sreenivasachary, N. J. Chem. Soc. Chem. Commun. 2000, 503; Kotha, S.; Halder, S.; Brahmachary, E.; Ganesh, T. Synlett 2000, 853; Kotha, S.; Sreenivasachary, N. Bioorg. Med. Chem. Lett. 1998, 8, 257; Kotha, S.; Sreenivasachary, N.; Brahmachary, E.; Tetrahedron Lett. 1998, 39, 2805.
45. For details of our earlier work dealing with olefin metathesis reaction see: Kotha, S.; Sreenivasachary, N.; Mohanraja, K.; Durani, S. Bioorg Med. Chem. Lett. 2001, 11, 1421; Kotha, S.; Sreenivasachary, N.; Brahmachary, E. Eur. J. Org. Chem. 2001, 787; Kotha, S.; Sreenivasachary, N. Eur. J. Org. Chem. 2001, 3375; Kotha, S.; Sreenivasachary, N. J. Chem. Soc. Chem. Commun. 2000, 503; Kotha, S.; Halder, S.; Brahmachary, E.; Ganesh, T. Synlett 2000, 853; Kotha, S.; Sreenivasachary, N. Bioorg. Med. Chem. Lett. 1998, 8, 257; Kotha, S.; Sreenivasachary, N.; Brahmachary, E.; Tetrahedron Lett. 1998, 39, 2805.
46. For details of our earlier work dealing with olefin metathesis reaction see: Kotha, S.; Sreenivasachary, N.; Mohanraja, K.; Durani, S. Bioorg Med. Chem. Lett. 2001, 11, 1421; Kotha, S.; Sreenivasachary, N.; Brahmachary, E. Eur. J. Org. Chem. 2001, 787; Kotha, S.; Sreenivasachary, N. Eur. J. Org. Chem. 2001, 3375; Kotha, S.; Sreenivasachary, N. J. Chem. Soc. Chem. Commun. 2000, 503; Kotha, S.; Halder, S.; Brahmachary, E.; Ganesh, T. Synlett 2000, 853; Kotha, S.; Sreenivasachary, N. Bioorg. Med. Chem. Lett. 1998, 8, 257; Kotha, S.; Sreenivasachary, N.; Brahmachary, E.; Tetrahedron Lett. 1998, 39, 2805.
47. For details of our earlier work dealing with olefin metathesis reaction see: Kotha, S.; Sreenivasachary, N.; Mohanraja, K.; Durani, S. Bioorg Med. Chem. Lett. 2001, 11, 1421; Kotha, S.; Sreenivasachary, N.; Brahmachary, E. Eur. J. Org. Chem. 2001, 787; Kotha, S.; Sreenivasachary, N. Eur. J. Org. Chem. 2001, 3375; Kotha, S.; Sreenivasachary, N. J. Chem. Soc. Chem. Commun. 2000, 503; Kotha, S.; Halder, S.; Brahmachary, E.; Ganesh, T. Synlett 2000, 853; Kotha, S.; Sreenivasachary, N. Bioorg. Med. Chem. Lett. 1998, 8, 257; Kotha, S.; Sreenivasachary, N.; Brahmachary, E.; Tetrahedron Lett. 1998, 39, 2805.
48. For details of our earlier work dealing with olefin metathesis reaction see: Kotha, S.; Sreenivasachary, N.; Mohanraja, K.; Durani, S. Bioorg Med. Chem. Lett. 2001, 11, 1421; Kotha, S.; Sreenivasachary, N.; Brahmachary, E. Eur. J. Org. Chem. 2001, 787; Kotha, S.; Sreenivasachary, N. Eur. J. Org. Chem. 2001, 3375; Kotha, S.; Sreenivasachary, N. J. Chem. Soc. Chem. Commun. 2000, 503; Kotha, S.; Halder, S.; Brahmachary, E.; Ganesh, T. Synlett 2000, 853; Kotha, S.; Sreenivasachary, N. Bioorg. Med. Chem. Lett. 1998, 8, 257; Kotha, S.; Sreenivasachary, N.; Brahmachary, E.; Tetrahedron Lett. 1998, 39, 2805.
49. For details of our earlier work dealing with olefin metathesis reaction see: Kotha, S.; Sreenivasachary, N.; Mohanraja, K.; Durani, S. Bioorg Med. Chem. Lett. 2001, 11, 1421; Kotha, S.; Sreenivasachary, N.; Brahmachary, E. Eur. J. Org. Chem. 2001, 787; Kotha, S.; Sreenivasachary, N. Eur. J. Org. Chem. 2001, 3375; Kotha, S.; Sreenivasachary, N. J. Chem. Soc. Chem. Commun. 2000, 503; Kotha, S.; Halder, S.; Brahmachary, E.; Ganesh, T. Synlett 2000, 853; Kotha, S.; Sreenivasachary, N. Bioorg. Med. Chem. Lett. 1998, 8, 257; Kotha, S.; Sreenivasachary, N.; Brahmachary, E.; Tetrahedron Lett. 1998, 39, 2805.