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Volumn 53, Issue 48, 1997, Pages 16435-16448

Sequential application of stereoselective syn-oxidation methodologies to natural product synthesis: A potentially biomimetic approach to the C12-C21 bistetrahydrofuran region of monensin

Author keywords

[No Author keywords available]

Indexed keywords

MONENSIN; TETRAHYDROFURAN DERIVATIVE;

EID: 0030775284     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01026-0     Document Type: Conference Paper
Times cited : (22)

References (56)
  • 14
    • 2542433188 scopus 로고
    • b) A similar reaction catalyzed by ruthenium tetraoxide / periodate appears to be stereospecific regarding alkene addition, but is less stereoselective affording a 3 : 1 mixture of cis-and trans-tetrahydrofurans favoring 15. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
    • (1981) J. Org. Chem. , vol.46 , pp. 3936
    • Carlsen, P.H.J.1    Katsuki, T.2    Martin, V.S.3    Sharpless, K.B.4
  • 36
    • 0002074345 scopus 로고
    • We originally attributed this regioselective outcome to additional steric hindrance provided by the ethyl substituent of triene substrate 19. However, the asymmetric dihydroxylation of triene i also provided a 5 : 1 mixture of dihydroxylation products ii and iii, and dihydroxylation of the internal trisubstituted alkene of i was not observed. Presumably the internal trisubstituted alkenes of substrates 19 and i are protected from dihydroxylation by polyene folding in the protic solvent medium. See also: Van Tamelen, E. E.; Sharpless, K. B. Tetrahedron Lett. 1967, 2655. Chemical equations presented.
    • (1967) Tetrahedron Lett. , pp. 2655
    • Van Tamelen, E.E.1    Sharpless, K.B.2
  • 37
    • 0343365528 scopus 로고    scopus 로고
    • note
    • Initial attempts to achieve syn-oxidative cyclization by reaction of diol-alkene 26 with acylperrhenate reagents were unsuccessful and appeared to give product iv as a single diastereomer. This unexpected product presumably arises from secondary alcohol oxidation and acid-catalyzed pinacol-type rearrangement. The principal difference between substrate 26 and other substrates which we had previously successfully cyclized (ref. 12) appears to be the presence of the tertiary hydroxyl group. Chemical equations presented.
  • 39
    • 0342496048 scopus 로고    scopus 로고
    • note
    • 17 (8 : 1 selectivity) as the result of chelate-controlled hydride addition (note that the ethyl substituent exerts a greater steric effect than the ring methylene). Reduction of 27 with sodium borohydride alone exhibited no stereoselectivity.
  • 40
    • 0029860777 scopus 로고    scopus 로고
    • The first highly enantioselective epoxidations of trans-alkenes bearing only aliphatic substituents were reported only recently: Tu, Y.; Wang, Z.-W.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9806
    • Tu, Y.1    Wang, Z.-W.2    Shi, Y.3
  • 41
    • 0039024095 scopus 로고
    • Manganese salen and porphyrin epoxidation catalysts give poor enantioselectivities with alkenes other than those bearing aryl, alkenyl, or alkynyl substituents. Reviews: a) Schurig, V.; Betschinger, F. Chem. Rev. 1992, 92, 873.
    • (1992) Chem. Rev. , vol.92 , pp. 873
    • Schurig, V.1    Betschinger, F.2
  • 48
    • 0000705946 scopus 로고
    • Stereospecific anti-polycyclizations of cyclic sulfates (prepared from dienes and trienes by asymmetric poly-dihydroxylation followed by poly-l,2-sulfate formation) have also been reported: Beauchamp, T. J.; Powers, J. P.; Rychnovsky, S. D. J. Am. Chem. Soc. 1995, 117, 12873.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 12873
    • Beauchamp, T.J.1    Powers, J.P.2    Rychnovsky, S.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.