Further evidence on the PET cyclization of α-silylmethylamines tethered with non-activated olefins: Demonstration by the total synthesis of (-)-retronecanol

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2285-2288

  Pandey, Ganesh ^a   Chakrabarti, Debasish ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIZIDINE DERIVATIVE; RETRONECANOL; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029925315     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00244-4     Document Type: Article

References (19)

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4. Jeon, Y. T.; Lee, C-P.; Mariano, P. S. J. Am. Chem. Soc.,1991, 113, 8847-8863.; Hasegawa, E.; Xu, W.; Mariano, P. S.; Yoon, U-C.; Kim, J-U. J. Am. Chem. Soc., 1988, 110, 8099-8111.
5. For reviews on indolizidine, pyrrolizidine and quinolizidine alkaloids see: Howard, A. S. and Michael, J. P. in The Alkaloids. Chemistry and Pharmacology, Brossi, A. Ed.; Academic Press, New York, 1986, 28, ch.3; Stevens, R. V. , in The Total Synthesis of Natural Products, Apsimon, A., Ed.;Wiley, New York, 1977, 3, 439; Nishimura, Y., in Studies in Natural Product Chemistry, Rahman, A. U. Ed; Elsevier, Amsterdam, 1988, 1, 227; and references cited therein.
6. For reviews on indolizidine, pyrrolizidine and quinolizidine alkaloids see: Howard, A. S. and Michael, J. P. in The Alkaloids. Chemistry and Pharmacology, Brossi, A. Ed.; Academic Press, New York, 1986, 28, ch.3; Stevens, R. V. , in The Total Synthesis of Natural Products, Apsimon, A., Ed.;Wiley, New York, 1977, 3, 439; Nishimura, Y., in Studies in Natural Product Chemistry, Rahman, A. U. Ed; Elsevier, Amsterdam, 1988, 1, 227; and references cited therein.
7. For reviews on indolizidine, pyrrolizidine and quinolizidine alkaloids see: Howard, A. S. and Michael, J. P. in The Alkaloids. Chemistry and Pharmacology, Brossi, A. Ed.; Academic Press, New York, 1986, 28, ch.3; Stevens, R. V. , in The Total Synthesis of Natural Products, Apsimon, A., Ed.;Wiley, New York, 1977, 3, 439; Nishimura, Y., in Studies in Natural Product Chemistry, Rahman, A. U. Ed; Elsevier, Amsterdam, 1988, 1, 227; and references cited therein.
8. Pandey, G.; Reddy, G. D. Tetrahedron Lett., 1992, 33, 6533-6536.
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10. Mariano etal mentioned in their paper that they repeated our work using λ>240nm wavelength whereas we have clearly mentioned that our cyclizations are carried out utilizing Pyrex filtered light (λ>280nm.)
11. Pandey, G.; Reddy, G. D.; Chakrabarti, D. J. Chem. Soc. Perk. Trans 1, 1995, 0000
12. For isolation, extraction, structural determination and biological importance of (-)-retronecanol and other Senecio alkaloids see Leonard N. J.; In The Alkaloid Chemistry and Physiology; Manske R. H. F. Ed.; Academic Press: New York, 1960, 6, pp. 37-121.
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15. ++1), 196, 172, 140 (100%), 122, 73, 55.
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17. +), 140, 124, 99, 97, 82, 69, 55 (100%), 51.
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