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Volumn 72, Issue 14, 2007, Pages 5374-5379

Diastereodivergent strategies for the synthesis of homochiral aculeatins

Author keywords

[No Author keywords available]

Indexed keywords

CHIRALITY; ORGANIC COMPOUNDS; SEPARATION; STEREOSELECTIVITY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 34447311920     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0707986     Document Type: Article
Times cited : (49)

References (30)
  • 2
    • 0035426033 scopus 로고    scopus 로고
    • Heilmann, J, Brun, R, Mayr, S, Rali, T, Sticher, O. Phytochemistry 2001, 57, 1281-1285. The relative configurations assigned for aculeatins A and B were erroneously assigned from the initial paper (see ref 1a) and have been corrected by Marco and co-workers see ref 5a
    • (b) Heilmann, J.; Brun, R.; Mayr, S.; Rali, T.; Sticher, O. Phytochemistry 2001, 57, 1281-1285. The relative configurations assigned for aculeatins A and B were erroneously assigned from the initial paper (see ref 1a) and have been corrected by Marco and co-workers (see ref 5a).
  • 11
    • 0001196589 scopus 로고    scopus 로고
    • (a) Mahrwald, R. Chem. Rev. 1999, 99, 1095-1120.
    • (1999) Chem. Rev , vol.99 , pp. 1095-1120
    • Mahrwald, R.1
  • 13
    • 0033575415 scopus 로고    scopus 로고
    • For examples of acyclic 1,3-anti induction in Mukaiyama aldol coupling using BF3·OEt2 as Lewis acid, see (a) Evans, D. A, Trotter, B. W, Coleman, P. J, Côté, B, Dias, L. C, Rajapakse, H. A, Tyler, A. N. Tetrahedron 1999, 55, 8671-8726
    • 2 as Lewis acid, see (a) Evans, D. A.; Trotter, B. W.; Coleman, P. J.; Côté, B.; Dias, L. C.; Rajapakse, H. A.; Tyler, A. N. Tetrahedron 1999, 55, 8671-8726.
  • 17
    • 15044358964 scopus 로고    scopus 로고
    • 2 involving a merge 1,2 and 1,3-induction, see Restorp, P.; Somfai, P. Org. Lett. 2005, 7, 893-895.
    • 2 involving a merge 1,2 and 1,3-induction, see Restorp, P.; Somfai, P. Org. Lett. 2005, 7, 893-895.
  • 20
    • 34447330570 scopus 로고    scopus 로고
    • 19F NMR spectra (500 MHz and 472 MHz, respectively). In our hands and with both NMR techniques, only one isomer can be detected (see Supporting Information).
    • 19F NMR spectra (500 MHz and 472 MHz, respectively). In our hands and with both NMR techniques, only one isomer can be detected (see Supporting Information).
  • 21
    • 34447325781 scopus 로고    scopus 로고
    • 1H NMR of the crude mixture.
    • 1H NMR of the crude mixture.
  • 27
    • 33746375063 scopus 로고    scopus 로고
    • For a recent characterization of a stable phenoxonium cation by crystal structure, see
    • For a recent characterization of a stable phenoxonium cation by crystal structure, see Lee, S. B.; Willis, A. C.; Webster, R. D. J. Am. Chem. Soc. 2006, 128, 9332-9333.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 9332-9333
    • Lee, S.B.1    Willis, A.C.2    Webster, R.D.3
  • 28
    • 0034647499 scopus 로고    scopus 로고
    • For interesting nitrogen versions of phenolic oxidation involving trapping of phenoxonium cation by sp2 or sp heteroatoms, see (a) Braun, N. A, Ousmer, M, Bray, J. D, Bouchu, D, Peters, K, Peters, E.-M, Ciufolini, M. A. J. Org. Chem. 2000, 65, 4397-4408
    • 2 or sp heteroatoms, see (a) Braun, N. A.; Ousmer, M.; Bray, J. D.; Bouchu, D.; Peters, K.; Peters, E.-M.; Ciufolini, M. A. J. Org. Chem. 2000, 65, 4397-4408.
  • 30
    • 33846072975 scopus 로고    scopus 로고
    • For the participation of a methoxy group as nucleophile for the synthesis of bis-spiroketal by trapping ring oxocarbenium species, see Li, Y, Zhou, F, Forsyth, C. J. Angew. Chem, Int. Ed. 2007, 46, 279-282
    • For the participation of a methoxy group as nucleophile for the synthesis of bis-spiroketal by trapping ring oxocarbenium species, see Li, Y.; Zhou, F.; Forsyth, C. J. Angew. Chem., Int. Ed. 2007, 46, 279-282.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.