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Volumn 74, Issue 11, 2009, Pages 4429-4433

Straightforward stereoselective access to cyclic peptidomimetics

Author keywords

[No Author keywords available]

Indexed keywords

AMINO GROUP; CHEMICAL EQUATIONS; CYCLIC DIPEPTIDE; PEPTIDOMIMETICS; QUATERNARY CENTERS; STEREO-SELECTIVE; STEREOSELECTIVE CONSTRUCTION; SYNTHETIC ROUTES; TRIPEPTIDE;

EID: 66249139880     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900679c     Document Type: Article
Times cited : (34)

References (52)
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    • For reviews, see: (j)
    • For reviews, see: (j) Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431-7448.
    • (2001) Tetrahedron , vol.57 , pp. 7431-7448
    • Souers, A.J.1    Ellman, J.A.2
  • 36
    • 53849110901 scopus 로고    scopus 로고
    • The use of metathesis reactions in peptidomimetic synthesis has been recently reviewed; see
    • The use of metathesis reactions in peptidomimetic synthesis has been recently reviewed; see: (a) Brik, A. Adv. Synth. Catal. 2008, 350, 1661-1675.
    • (2008) Adv. Synth. Catal. , vol.350 , pp. 1661-1675
    • Brik, A.1
  • 42
    • 0000453017 scopus 로고
    • Related chiral templates such as Williams' diphenyloxazinones have also been used in the synthesis of quaternary amino acids; see
    • Related chiral templates such as Williams' diphenyloxazinones have also been used in the synthesis of quaternary amino acids; see: Williams, R. M.; Zhai, W. Tetrahedron 1988, 44, 5425-5430.
    • (1988) Tetrahedron , vol.44 , pp. 5425-5430
    • Williams, R.M.1    Zhai, W.2
  • 44
    • 66249138715 scopus 로고    scopus 로고
    • note
    • The configuration of the new stereogenic center was assumed as depicted according to previous results (see ref 10) and confirmed in subsequent transformations carried out. Moreover, the stereochemical integrity was preserved in the Grignard addition step as determined by chiral HPLC analysis of compounds 4.
  • 45
    • 17444389675 scopus 로고    scopus 로고
    • A diastereoselective radical addition of alkyl groups to iminolactones 3 was also reported; see
    • A diastereoselective radical addition of alkyl groups to iminolactones 3 was also reported; see: Miyabe, H.; Yamaoka, Y.; Takemoto, Y. J. Org. Chem. 2005, 70, 3324-3327.
    • (2005) J. Org. Chem. , vol.70 , pp. 3324-3327
    • Miyabe, H.1    Yamaoka, Y.2    Takemoto, Y.3
  • 46
    • 33846138331 scopus 로고    scopus 로고
    • For the synthesis of a trifluoromethyl analogue of 4c, see
    • For the synthesis of a trifluoromethyl analogue of 4c, see: Chaume, G.; Van Severen, M.-C.; Marinkovic, S.; Brigaud, T. Org. Lett. 2006, 8, 6123-6126.
    • (2006) Org. Lett. , vol.8 , pp. 6123-6126
    • Chaume, G.1    Van Severen, M.-C.2    Marinkovic, S.3    Brigaud, T.4
  • 47
    • 66249104543 scopus 로고    scopus 로고
    • note
    • 4, Grubbs-Hoveyda catalyst, or heating under microwave irradiation. In all cases the starting material was recovered unchanged.
  • 48
    • 0035966178 scopus 로고    scopus 로고
    • Preparation of five-membered lactams fused with other rings by means of RCM are very scarce in the literature; see
    • Preparation of five-membered lactams fused with other rings by means of RCM are very scarce in the literature; see: (a) Lim, S. H.; Ma, S.; Beak, P. J. Org. Chem. 2001, 66, 9056-9062.
    • (2001) J. Org. Chem. , vol.66 , pp. 9056-9062
    • Lim, S.H.1    Ma, S.2    Beak, P.3
  • 50
    • 66249144555 scopus 로고    scopus 로고
    • note
    • Direct coupling of amine 4a with a N-Boc-protected dehydroalanine failed to provide a RCM precursor of compound 11. (Chemical Equation Presented)
  • 51
    • 66249127092 scopus 로고    scopus 로고
    • note
    • Base-mediated transesterification or hydrogenolysis at high pressure of the lactone ring in 12 failed to give the corresponding hydroxy ester or hydroxy acid.
  • 52
    • 0028867825 scopus 로고
    • Related seven-membered lactams were prepared by Holmes and coworkers, although lacking the quaternary center. In their work, the cis diastereoisomer had an extended conformation, whereas the trans isomer formed a β-turn structure. See
    • Related seven-membered lactams were prepared by Holmes and coworkers, although lacking the quaternary center. In their work, the cis diastereoisomer had an extended conformation, whereas the trans isomer formed a β-turn structure. See: Nadin, A.; Derrer, S.; McGeary, R. P.; Goodman, J. M.; Raithby, P. R.; Holmes, A. B.; O'Hanlon, P. J.; Pearson, N. D. J. Am. Chem. Soc. 1995, 117, 9768-9769.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9768-9769
    • Nadin, A.1    Derrer, S.2    McGeary, R.P.3    Goodman, J.M.4    Raithby, P.R.5    Holmes, A.B.6    O'Hanlon, P.J.7    Pearson, N.D.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.