An efficient ring-closing metathesis reaction of geminally disubstituted olefins using first generation Grubbs' catalyst: Enantiospecific synthesis of pacifigorgianes

Tetrahedron Letters

Volumn 44, Issue 42, 2003, Pages 7817-7820

  Srikrishna, A ^a   Dethe, Dattatraya H ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYL GROUP; SESQUITERPENE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CIS ISOMER; ENANTIOSELECTIVITY; RING CLOSING METATHESIS; TRANS ISOMER;

EID: 0141794006     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.076     Document Type: Article

References (16)

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5. To the best of our knowledge there are only very few reports on the synthesis of trisubstituted olefins by RCM reaction of dienes using the catalyst 1 . For example, in our laboratory, under a variety of conditions, catalyst 1 failed to induce the RCM reaction in the diene I . For a systematic study, see: (a) Kirkland, T. A.; Grubbs, R. H. J. Org. Chem. 1997, 62, 7310-7318. See also: (b) Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312-11313.
6. To the best of our knowledge there are only very few reports on the synthesis of trisubstituted olefins by RCM reaction of dienes using the catalyst 1 . For example, in our laboratory, under a variety of conditions, catalyst 1 failed to induce the RCM reaction in the diene I . For a systematic study, see: (a) Kirkland, T. A.; Grubbs, R. H. J. Org. Chem. 1997, 62, 7310-7318. See also: (b) Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312-11313.
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9. For a similar entropic effect in rhodium carbenoid C=H insertion reaction, see: (b) Srikrishna, A.; Gharpure, S. J. Chem. Commun. 1998, 1589-1590.
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15. So far only one report each on the synthesis of pacifigorgiol and tamariscol have been reported. See: (a) Martin, M.; Clardy, J. Pure Appl. Chem. 1982, 54, 1915-1918; (b) Tori, M.; Sono, M.; Nishigaki, Y.; Nakashima, K.; Asakawa, Y. J. Chem. Soc., Perkin Trans. 1 1991, 435-445.
16. So far only one report each on the synthesis of pacifigorgiol and tamariscol have been reported. See: (a) Martin, M.; Clardy, J. Pure Appl. Chem. 1982, 54, 1915-1918; (b) Tori, M.; Sono, M.; Nishigaki, Y.; Nakashima, K.; Asakawa, Y. J. Chem. Soc., Perkin Trans. 1 1991, 435-445.