메뉴 건너뛰기




Volumn , Issue 5, 2005, Pages 854-863

Hormaomycin analogues by precursor-directed biosynthesis - Synthesis of and feeding experiments with amino acids related to the unique 3-(trans-2′- nitrocyclopropyl)alanine constituent

Author keywords

Aldol reactions; Amino acids; Biosynthesis; Hormaomycin; Isotopic labeling; Natural products; Synthetic methods

Indexed keywords

3 (2' AMINOCYCLOPROPYL)ALANINE; 3 (2' NITROCYCLOPROPYL)ALANINE; 3 [2 (HYDROXYCARBONYL)CYCLOPROPYL]ALANINE; 3 [2 (METHOXYCARBONYL)CYCLOPROPYL]ALANINE; DEUTERIUM; GLYCINE DERIVATIVE; HORMAOMYCIN; LACTONE; LITHIUM DERIVATIVE; NATURAL PRODUCT; NORVALINE; PEPTIDE; TERT BUTYL (DIPHENYLMETHYLENE)AMINOACETATE; UNCLASSIFIED DRUG;

EID: 15044338608     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400608     Document Type: Article
Times cited : (18)

References (60)
  • 3
    • 0012318137 scopus 로고
    • b) E. Rössner, A. Zeeck, W. A. König, Angew. Chem. 1990, 102, 84-85; Angew. Chem. Int. Ed. Engl. 1990, 29, 64-65;
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 64-65
  • 7
    • 9244260150 scopus 로고    scopus 로고
    • The formula of 1a as presented here and in these previous publications do depict the correct configuration in the (S)-isoleucine (He) moiety. The formulas in our recently published "Corrigendum" (see Chem. Eur. J. 2004, 10, 5568) were indeed erroneous in this respect.
    • (2004) Chem. Eur. J. , vol.10 , pp. 5568
  • 17
    • 15044349562 scopus 로고
    • Dissertation, University of Göttingen
    • e) J. Zindel, Dissertation, University of Göttingen, 1993.
    • (1993)
    • Zindel, J.1
  • 19
    • 0141853177 scopus 로고    scopus 로고
    • This strategy was recently applied for the preparation of enantiomerically pure 4, which in turn was used in the total synthesis of 2 (see ref. [2e]); b) A. Armstrong, J. N. Scutt, Org. Lett. 2003, 5, 2331-2334.
    • (2003) Org. Lett. , vol.5 , pp. 2331-2334
    • Armstrong, A.1    Scutt, J.N.2
  • 22
    • 0029985979 scopus 로고    scopus 로고
    • and references cited therein
    • a) C. Hamon, B. J. Rawlings, Synth. Commun. 1996, 26, 1109-1116, and references cited therein.
    • (1996) Synth. Commun. , vol.26 , pp. 1109-1116
    • Hamon, C.1    Rawlings, B.J.2
  • 23
    • 0000234063 scopus 로고    scopus 로고
    • This compound was prepared by alkylation of the lithiated O'Donnel's glycine equivalent 11 with iodomethylcyclopropane followed by acid-catalyzed deprotection, see also: b) E. J. Corey, F. Xu, M. C. Noe, J. Am. Chem. Soc. 1997, 119, 12414-12415;
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12414-12415
    • Corey, E.J.1    Xu, F.2    Noe, M.C.3
  • 27
    • 0002076066 scopus 로고    scopus 로고
    • and ref.[3] cited therein
    • b) for recent reviews see: M. J. O'Donnell, Aldrichimica Acta 2001, 34, 3-15, and ref.[3] cited therein.
    • (2001) Aldrichimica Acta , vol.34 , pp. 3-15
    • O'Donnell, M.J.1
  • 28
    • 0029010820 scopus 로고
    • Several of the conceivable approaches to 4 such as the Curtius degradation of protected 3-(trans-2-hydroxycarbonylcyclopropyl)alanine as well as substitution of the 3-[trans-2-(tert-butoxycarbonyl)aminocyclopropyl]methanol tosylate with the nucleophilic O'Donnell glycine equivalent 11 were tested without any success. The starting materials for these attempted transformations were prepared from dimethyl trans-1,2-cyclopropanedicarboxylate according to published procedures. Cf. a) R. Csuk, Y. v. Scholz, Tetrahedron 1995, 51, 7193-7206;
    • (1995) Tetrahedron , vol.51 , pp. 7193-7206
    • Csuk, R.1    Scholz, Y.V.2
  • 40
    • 15044351261 scopus 로고    scopus 로고
    • Dissertation, University of Göttingen
    • For experimental details see: P. Alvermann, Dissertation, University of Göttingen, 2001.
    • (2001)
    • Alvermann, P.1
  • 43
    • 15044347479 scopus 로고    scopus 로고
    • note
    • 1H-NMR spectra. Moreover, at least for one hormaomycin analogue, 1H-NMR spectra measured with the same spectrometer, in the same solvent, at the same temperature, and from the same sample showed distinct differences. See ref.[1d] for a deeper discussion.
  • 45
    • 0041812777 scopus 로고    scopus 로고
    • (Ed.: A. de Meijere), Thieme, Stuttgart
    • b) J. C. Walton, in Methods of Organic Chemistry (Houben-Weyl), vol. E17c (Ed.: A. de Meijere), Thieme, Stuttgart, 1997, pp. 2438-2525.
    • (1997) Methods of Organic Chemistry (Houben-Weyl) , vol.E17C , pp. 2438-2525
    • Walton, J.C.1
  • 51
    • 15044360753 scopus 로고    scopus 로고
    • note
    • In the radical homoallylic rearrangement of hypoglycine A the arising intermediate inactivates general Acyl-CoA Dehydrogenase, see ref.[20]
  • 54
    • 15044357327 scopus 로고    scopus 로고
    • note
    • a) For spectroscopic and analytical data of the non-deuterated compound see refs.[3d,4];
  • 55
    • 0028220912 scopus 로고
    • b) for another method of preparation of a non-deuterated compound see also: L. Dechoux, E. Doris, Tetrahedron Lett. 1994, 35, 2017-2020.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 2017-2020
    • Dechoux, L.1    Doris, E.2
  • 56
    • 15044354826 scopus 로고    scopus 로고
    • note
    • a) For spectroscopic and analytical data of the non-deuterated compound see refs.[3e,9a];
  • 57
    • 15044365970 scopus 로고    scopus 로고
    • note
    • b) for another method of preparation of the non-deuterated compound see refs.[9a,9b]
  • 58
    • 15044340522 scopus 로고    scopus 로고
    • note
    • For spectroscopic and analytical data of the non-deuterated compound see ref.[3a]
  • 59
    • 15044364054 scopus 로고    scopus 로고
    • note
    • For spectroscopic and analytical data of the non-deuterated compound see Supporting Information in ref.[4b]
  • 60
    • 15044355822 scopus 로고    scopus 로고
    • note
    • For spectroscopic and analytical data of the non-deuterated compound see ref.[4c] and Supporting Information in ref.[4b]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.