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Volumn 53, Issue 27, 1997, Pages 9169-9202

Enantioselective total synthesis of (-)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step

Author keywords

[No Author keywords available]

Indexed keywords

DENTICULATIN; NATURAL PRODUCT; UNCLASSIFIED DRUG;

EID: 0030925011     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00617-0     Document Type: Article
Times cited : (24)

References (59)
  • 7
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    • Morrison, J. D., Ed.; Academic Press: New-York, Chapter 2
    • For some reviews, see: (a) Evans, D. A. in Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New-York, 1984; Vol. 3., Chapter 2.
    • (1984) Asymmetric Synthesis , vol.3
    • Evans, D.A.1
  • 18
    • 0001524453 scopus 로고
    • The first total synthesis generated a mixture of denticulatin A and B, see: Ziegler, F. E.; Becker, M. R. J. Org. Chem. 1990, 55, 2800.
    • (1990) J. Org. Chem. , vol.55 , pp. 2800
    • Ziegler, F.E.1    Becker, M.R.2
  • 19
    • 0030041247 scopus 로고    scopus 로고
    • For the first stereoselective synthesis of denticulatin B, see: Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811.
    • (1996) Tetrahedron , vol.52 , pp. 1811
    • Paterson, I.1    Perkins, M.V.2
  • 24
    • 0002736658 scopus 로고
    • (a) Reviews dealing with chain desymmetrizations: Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9; Magnuson, S. R. Tetrahedron 1995, 51, 2167.
    • (1994) Acc. Chem. Res. , vol.27 , pp. 9
    • Poss, C.S.1    Schreiber, S.L.2
  • 25
    • 0028799792 scopus 로고
    • (a) Reviews dealing with chain desymmetrizations: Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9; Magnuson, S. R. Tetrahedron 1995, 51, 2167.
    • (1995) Tetrahedron , vol.51 , pp. 2167
    • Magnuson, S.R.1
  • 26
    • 0029938866 scopus 로고    scopus 로고
    • (b) For an elegant approach towards the synthesis of polypropionate fragments via a kinetic desymmetrization of polycyclic systems, see: Marchionni, C.; Vogel, P.; Roversi, P. Tetrahedron Lett. 1996, 37, 4149.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4149
    • Marchionni, C.1    Vogel, P.2    Roversi, P.3
  • 27
    • 0001579832 scopus 로고
    • Preparation of meso dialdehyde 6 and its desymmetrization by olefination with a chiral phosphonate: Kann, N.; Rein, T. J. Org. Chem. 1993, 58, 3802.
    • (1993) J. Org. Chem. , vol.58 , pp. 3802
    • Kann, N.1    Rein, T.2
  • 28
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    • Prepared according to ref. 12
    • Prepared according to ref. 12.
  • 29
    • 0000784039 scopus 로고
    • and references cited therein
    • Roush, W. R. J. Org. Chem. 1991, 56, 4151 and references cited therein.
    • (1991) J. Org. Chem. , vol.56 , pp. 4151
    • Roush, W.R.1
  • 31
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    • The formation of thioglycosides with 1,2-ethanedithiol in this type of reaction has been observed previously: (a) Askin, D.; Angst, C.; Danishefsky, S. J. Org. Chem. 1987, 52, 622.
    • (1987) J. Org. Chem. , vol.52 , pp. 622
    • Askin, D.1    Angst, C.2    Danishefsky, S.3
  • 34
    • 0343883864 scopus 로고    scopus 로고
    • note
    • Changing to organocerium compounds or adding HMPA or TMEDA to the reaction medium did not have any effect on the addition.
  • 37
    • 0343448003 scopus 로고    scopus 로고
    • note
    • Reduction with diisobutylaluminum hydride or lithium aluminumhydride gave concomminant deprotection of the silyl protecting group.
  • 46
    • 0343012446 scopus 로고    scopus 로고
    • note
    • 7 They describe the synthesis of aldehyde 3 in 80% ee, via alcohol 26 obtained from kinetically resolved (R)-2-methyl-1-penten-3-ol. Furthermore, a sample of 26 oxidized to aldehyde 3 with pyridinium chlorochromate and reduced back to the same alcohol showed no racemization during this process.
  • 47
    • 84958315401 scopus 로고
    • The chlorotitanium enolates were generated by the standard procedure reported by: Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpí, F. J. Am. Chem. Soc. 1991, 113, 1047. These substrates exhibit the stereochemical attributes of Z(O)-enolates.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 1047
    • Evans, D.A.1    Rieger, D.L.2    Bilodeau, M.T.3    Urpí, F.4
  • 54
    • 0343883861 scopus 로고    scopus 로고
    • note
    • It was mentioned that also the nature of the protecting group of the β-oxygen bearing substituent plays a significant role, giving an attenuation of 1,3-stereoinduction with a t-butyldimethylsilyl protecting group relative to a p-methoxybenzyl ether: see ref. 31b.
  • 55
    • 0343012443 scopus 로고    scopus 로고
    • note
    • We are indebted to Dr. Ian Paterson for kindly providing reference spectra and experimental details.
  • 58
    • 0343447999 scopus 로고    scopus 로고
    • note
    • 7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.