메뉴 건너뛰기




Volumn 71, Issue 25, 2006, Pages 9411-9419

Ring closing metathesis/fragmentation route to (Z)-configured medium ring cycloalkenes. Total synthesis of (±)-periplanone C

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MODIFICATION; FREE RADICALS; HORMONES; NEGATIVE IONS; SYNTHESIS (CHEMICAL);

EID: 33845527881     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061790j     Document Type: Article
Times cited : (21)

References (88)
  • 3
    • 0542397750 scopus 로고    scopus 로고
    • Review articles
    • Review articles: (a) Molander, G. Acc. Chem. Res. 1998, 31, 603.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 603
    • Molander, G.1
  • 4
    • 0026721571 scopus 로고
    • Eight-Membered carbocycles
    • Eight-Membered carbocycles: (b) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
    • (1992) Tetrahedron , vol.48 , pp. 5757
    • Petasis, N.A.1    Patane, M.A.2
  • 6
    • 0002174828 scopus 로고
    • Eight-and nine-membered carbocycles: Atta-ur-Rahman, Ed.; Eisevier: Amsterdam
    • Eight-and nine-membered carbocycles: (d) Oishi, T.; Ohtsuka, Y. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Eisevier: Amsterdam, 1989; Vol. 3, p 73.
    • (1989) Studies in Natural Products Synthesis , vol.3 , pp. 73
    • Oishi, T.1    Ohtsuka, Y.2
  • 7
    • 0028893499 scopus 로고
    • Lactones
    • Lactones: (e) Rousseau, G. Tetrahedron 1995, 51, 2777.
    • (1995) Tetrahedron , vol.51 , pp. 2777
    • Rousseau, G.1
  • 8
    • 0034246704 scopus 로고    scopus 로고
    • Yet, L. Chem. Rev. 2000, 100, 2963.
    • (2000) Chem. Rev. , vol.100 , pp. 2963
    • Yet, L.1
  • 9
    • 0033618523 scopus 로고    scopus 로고
    • Review articles on radical methods: (a) Yet, L. Tetrahedron 1999, 55, 9349.
    • (1999) Tetrahedron , vol.55 , pp. 9349
    • Yet, L.1
  • 11
    • 3343012187 scopus 로고    scopus 로고
    • Reviews on the development and various applications of the alkene metathesis reaction: (a) Grubbs, R. H. Tetrahedron 2004, 60, 7117.
    • (2004) Tetrahedron , vol.60 , pp. 7117
    • Grubbs, R.H.1
  • 16
    • 0032580376 scopus 로고    scopus 로고
    • For review articles on RCM, see
    • For review articles on RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 19
    • 0034674322 scopus 로고    scopus 로고
    • For a short review on the application of RCM in the synthesis of medium-sized rings, see: (a) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2073
    • Maier, M.E.1
  • 32
    • 0035859315 scopus 로고    scopus 로고
    • 12-Membered rings
    • 12-Membered rings: (i) Snider, B. B.; Song, F. Org. Lett. 2001, 3, 1817.
    • (2001) Org. Lett. , vol.3 , pp. 1817
    • Snider, B.B.1    Song, F.2
  • 45
    • 0038373087 scopus 로고    scopus 로고
    • Corrigendum: Prunet, J. Angew. Chem., Int. Ed. 2003, 42, 3322
    • Prunet, J. Angew. Chem., Int. Ed. 2003, 42, 2826. Corrigendum: Prunet, J. Angew. Chem., Int. Ed. 2003, 42, 3322.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 2826
    • Prunet, J.1
  • 60
    • 33845529555 scopus 로고    scopus 로고
    • note
    • Other bases, such as DBU. NaH, or metal alkoxides, were not successful.
  • 61
    • 0000873998 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
    • However, examples are known where the fragmentation is successful even when this stereoelectronic requirement is not fulfilled; for a review article on Grob fragmentation, see: Weyerstahl, P.; Marschall, H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991: Vol. 6, p 1041.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 1041
    • Weyerstahl, P.1    Marschall, H.2
  • 62
    • 33845535353 scopus 로고    scopus 로고
    • note
    • Other bases, such as potassium ethoxide, potassium tert-butoxide, sodium hydride, DBU, potassium carbonate/18-crown-6. or potassium hydroxide/18-crown-6, were unsuccessful.
  • 63
    • 33845530045 scopus 로고    scopus 로고
    • note
    • In the case of compounds 3a-c, the bicyclic system is thermodynamically favored and the fragmentation step cannot be performed as a simple retro-aldol reaction.
  • 65
    • 33947482234 scopus 로고
    • See the Supporting Information for details
    • The stereochemistry of compounds 11 and 12 was established in the following way: on oxidation with PDC both 12 syn and 12 anti were converted into the same ketone (15): this compound was then subjected to hydrogenation of the alkene bond over Pd/C to give the trans-decalone derivative described in the literature: Wharton, P. S.; Hiegel, G. A. J. Org. Chem. 1965, 30, 3254. See the Supporting Information for details.
    • (1965) J. Org. Chem. , vol.30 , pp. 3254
    • Wharton, P.S.1    Hiegel, G.A.2
  • 66
    • 33845539393 scopus 로고    scopus 로고
    • note
    • These results were obtained with the stereochemically defined isomers 12 syn and 12 anti, purified by column chromatography and separately characterized. The whole sequence of reactions was also performed with the diastereomeric mixture, without the separation of the isomers, with similar results.
  • 79
    • 33845543169 scopus 로고    scopus 로고
    • note
    • In this case, the fragmentation step could be performed under radical conditions, which would require some additional steps though.
  • 80
    • 0042706825 scopus 로고    scopus 로고
    • A review article on the alkene (E)-(Z) isomerization: Dugave, C.; Demange, L. Chem. Rev. 2003, 103, 2475.
    • (2003) Chem. Rev. , vol.103 , pp. 2475
    • Dugave, C.1    Demange, L.2
  • 82
    • 0033484573 scopus 로고    scopus 로고
    • Triene 28 possesses four allylic hydrogen atoms sterically available for the abstraction, both electron-deficient (a to the carbonyl group) and electron-rich (a to the two-methylene group). For a review article on polarity reversal catalysis in hydrogen abstraction reactions, see: Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25.
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 25
    • Roberts, B.P.1
  • 87
    • 33845518217 scopus 로고    scopus 로고
    • note
    • 13C NMR spectrum identical to the spectrum previously reported in ref 34c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.