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Volumn 41, Issue 23, 2002, Pages 4573-4576

Asymmetric syntheses of pectenotoxins-4 and -8, Part II: Synthesis of the C20-C30 and C31-C40 subunits and fragment assembly

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; MACROLIDE; MARINE TOXIN; NATURAL PRODUCT; PECTENOTOXIN 4; PECTENOTOXIN 8; PECTENOTOXIN-4; PECTENOTOXIN-8; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 85047698843     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (83)

References (37)
  • 2
    • 0037011207 scopus 로고    scopus 로고
    • D. A. Evans, H. A. Rajapakse, D. Stenkamp, Angew. Chem. 2002, 114, 4751; Angew. Chem. Int. Ed. 2002, 41, 4569.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4569
  • 3
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    • note
    • A full account of this work will be published in due course.
  • 6
    • 85007652485 scopus 로고    scopus 로고
    • note
    • 2O = di-tert-butyl dicarbonate; LDA = lithium diisopropylamide; HMPA = hexamethylphosphoramide; TBODPS = tert-butoxydiphenylsilyl; RT= room temperature; TAS-F = tris(dimethyamino)sulfur(trimethylsilyl)difluoride.
  • 13
    • 0025073031 scopus 로고
    • T. Fukuyama, S.-L. Lin, L. Li, J. Am. Chem. Soc. 1990, 112, 7050-7051; see also; D. A. Evans, B. W. Trotter, P. J. Coleman, B. Cote, L. Carlos Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 7050-7051
    • Fukuyama, T.1    Lin, S.-L.2    Li, L.3
  • 15
    • 0025354154 scopus 로고
    • Conditions adapted from: M. Hartman, E. Zibral, Tetrahedron Lett. 1990, 31, 2875-2878. Both Wittig and Petersen conditions resulted in aldehyde decomposition with no observed product.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2875-2878
    • Hartman, M.1    Zibral, E.2
  • 20
    • 85007647941 scopus 로고    scopus 로고
    • note
    • No undesired tetrahydropyran byproducts were observed in this reaction.
  • 22
    • 0032537206 scopus 로고    scopus 로고
    • PMB deprotection with DDQ was incompatible with the pectenotoxin diene, as exclusive allylic oxidation was observed. For successful deprotections of PMB ethers in the presence of allylic dienes see: a) N. Murakami, W. Wang, M. Aoki, Y. Tsutsui, M. Sugimoto, M. Kobayashi, Tetrahedron Lett. 1998, 39, 2349-2352;
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2349-2352
    • Murakami, N.1    Wang, W.2    Aoki, M.3    Tsutsui, Y.4    Sugimoto, M.5    Kobayashi, M.6
  • 26
    • 85007646907 scopus 로고    scopus 로고
    • ref. [19b]
    • a) ref. [19b];
  • 28
    • 0035979030 scopus 로고    scopus 로고
    • b) D. A. Evans, D. M. Fitch, T. E. Smith, V. J. Cee, J. Am. Chem. Soc. 2000, 122, 10033-10046; A. B. Smith, B. M. Brandt, Org. Lett. 2001, 3, 1685-1688.
    • (2001) Org. Lett. , vol.3 , pp. 1685-1688
    • Smith, A.B.1    Brandt, B.M.2
  • 30
    • 85007646205 scopus 로고    scopus 로고
    • note
    • Initial feasibility studies on a model system revealed a dramatic counterion effect for this Julia coupling reaction. The use of KHMDS as the base resulted in a 29:71 ratio of C32 epimers favoring the undesired product. We attribute this epimerization side reaction to be due to ring-F cleavage through β-alkoxy elimination and readdition to the intermediate unsaturated sulfone.
  • 36
    • 85007633317 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of pectenotoxin-1, -4, and -8, as well as samples of pectenotoxin-1 and -8.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.