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Volumn 120, Issue 20, 1998, Pages 4916-4925

Total synthesis of (±)-methyl atis-16-en-19-oate via homoallyl- homoallyl radical rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENOID; METHYL ATIS 16 EN 19 OATE; TETRACYCLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032572056     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9739042     Document Type: Article
Times cited : (115)

References (47)
  • 10
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    • (b) Chen, K.; Shi, Q.; Fujioka, T.; Nakano, T.; Hu, C.-Q.; Jim, J.-Q.; Kilkuskie, R. E.; Lee, K.-H. Bioorg. Med. Chem. 1995, 3, 1345-1348. Total synthesis: Corey, E. J.; Liu, K. J. Am. Chem. Soc. 1997, 119, 9929-9930.
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    • Corey, E.J.1    Liu, K.2
  • 13
    • 37049079173 scopus 로고
    • and references therein
    • (a) Recent synthesis: Berettoni, M.; Chiara, G. D.; Iacoangeli, T.; Surdo, P. L.; Bettolo, R. M.; di Mirabello, L. M.; Nicolini, L.; Scarpelli, R. Helv. Chim. Acta 1996, 79, 2035-2041 and references therein, (b) Our own synthetic study: Ihara, M.; Toyota, M.; Fukumoto, K.; Kamitani, T. J. Chem. Soc., Perkin Trans. 1 1986, 2151-2161 and references therein.
    • (1986) J. Chem. Soc., Perkin Trans. 1 , pp. 2151-2161
    • Ihara, M.1    Toyota, M.2    Fukumoto, K.3    Kamitani, T.4
  • 15
    • 0009823616 scopus 로고
    • and references therein
    • Although a face-protonated, trachlobane-type intermediate is employed in ref 10, we prefer the bridged ions 2 and 3 that are now widely accepted, see: Coates, R. M.; Bertram, E. F. J. Org. Chem. 1971, 36, 3722-3729 and references therein.
    • (1971) J. Org. Chem. , vol.36 , pp. 3722-3729
    • Coates, R.M.1    Bertram, E.F.2
  • 17
    • 33748719845 scopus 로고    scopus 로고
    • and references therein
    • In some cases, the cyclopropylcarbinyl radical can be trapped to give the cyclopropane derivative. For example, see: Srikrishna, A.; Sharma, V. R. J. Chem. Soc., Perkin Trans. 1 1997, 177-181 and references therein.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 177-181
    • Srikrishna, A.1    Sharma, V.R.2
  • 18
    • 0000531841 scopus 로고
    • For reviews, see: (a) Nonhebel, D. C. Chem. Soc. Rev. 1993, 347-359. (b) Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115.
    • (1993) Chem. Soc. Rev. , pp. 347-359
    • Nonhebel, D.C.1
  • 19
    • 0042789931 scopus 로고
    • For reviews, see: (a) Nonhebel, D. C. Chem. Soc. Rev. 1993, 347-359. (b) Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115.
    • (1993) Chem. Rev. , vol.93 , pp. 2091-2115
    • Dowd, P.1    Zhang, W.2
  • 28
    • 0026006753 scopus 로고
    • and references therein
    • Larock, R. C.; Hightower, T. R.; Kraus, G. A.; Hahn, P.; Zheng, D. Tetrahedron Lett. 1995, 36, 2423-2426. For mechanistic studies, see: Larock, R. C.; Lee, N. H. Ibid. 1991, 42, 5911-5914 and references therein.
    • (1991) Tetrahedron Lett. , vol.42 , pp. 5911-5914
    • Larock, R.C.1    Lee, N.H.2
  • 29
    • 2642625829 scopus 로고    scopus 로고
    • To prove the effect of the solvent, we used HMPA (to give 15, 36%) and DMPU (to give 15, 45%) as polar solvents
    • To prove the effect of the solvent, we used HMPA (to give 15, 36%) and DMPU (to give 15, 45%) as polar solvents.
  • 33
    • 2642694865 scopus 로고    scopus 로고
    • note
    • 2,7]octane derivative IV and endo-olefin III was produced under these reaction conditions. (Matrix Presented) (Matrix Presented)
  • 34
    • 0001834924 scopus 로고
    • Liotta, D., Ed.; JAI Press: Greenwich, CT
    • Minimum energy structures were located by the global search program GMMX (Version 1.0) (Serena software, Bloomington, IN). The lowest energy structure 24C located in this fashion was then subjected to molecular mechanics minimization using the MMX force field (Gajewski, J. J.; Gilbert, K. E.; Mckelvey, J. In Advances in Molecular Modeling; Liotta, D., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 65-92) in the computer program PCMODEL (Version 5.01) (Serena software, Bloomington, IN). Finally, this molecular mechanics structure was reminimized by employing the PM3 model in the program MOPAC (Version 7.0) (Serena software, Bloomington, IN).
    • (1993) Advances in Molecular Modeling , vol.2 , pp. 65-92
    • Gajewski, J.J.1    Gilbert, K.E.2    Mckelvey, J.3
  • 38
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    • Mori, K.; Matsui, M. Tetrahedron Lett. 1966, 175-180; Tetrahedron 1968, 24, 3095-3111.
    • (1968) Tetrahedron , vol.24 , pp. 3095-3111
  • 42
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    • 2 from a β-oriented diazene intermediate (CH-N=NH)
    • 2 from a β-oriented diazene intermediate (CH-N=NH).
  • 44
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    • Although deoxygenation of the corresponding thiobenzoate, prepared from naturally occurring 12α-acetoxykaur-16-en-19-oic acid, was performed for degradation purposes, the reported product was (-)-kaurenoic acid (mass spectral analysis), see: Beale, M. H.; Bearder, J. R.; MacMillan, J.; Matsuo, A.; Phinney, B. O. Phytochemistry 1983, 22, 875-881.
    • (1983) Phytochemistry , vol.22 , pp. 875-881
    • Beale, M.H.1    Bearder, J.R.2    MacMillan, J.3    Matsuo, A.4    Phinney, B.O.5
  • 45
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    • See the Experimental Section of ref 17b
    • See the Experimental Section of ref 17b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.