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Volumn 63, Issue 26, 2007, Pages 5739-5753

Total synthesis of mycolactones A and B

Author keywords

Buruli ulcer; Mycolactones; Total synthesis

Indexed keywords

LACTONE DERIVATIVE; MACROLIDE; MYCOLACTONE A; MYCOLACTONE B; UNCLASSIFIED DRUG;

EID: 34248631378     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.057     Document Type: Article
Times cited : (29)

References (55)
  • 1
    • 34248632683 scopus 로고    scopus 로고
    • For a general review on Buruli ulcer, see:
  • 2
    • 0004321816 scopus 로고    scopus 로고
    • Asiedu K., Scherpbier R., and Ravinglione M. (Eds), World Health Organization, Geneva, Switzerland
    • In: Asiedu K., Scherpbier R., and Ravinglione M. (Eds). Buruli Ulcer: Mycobacterium ulcerans Infection (2000), World Health Organization, Geneva, Switzerland
    • (2000) Buruli Ulcer: Mycobacterium ulcerans Infection
  • 15
    • 34248669448 scopus 로고    scopus 로고
    • note
    • See Ref. 9b.
  • 25
    • 34248644463 scopus 로고    scopus 로고
    • note
    • A preliminary report of this work has been reported in Ref. 8.
  • 29
    • 0024840703 scopus 로고
    • Asymmetric dihydroxylation under the stoichiometric conditions gave a much higher selectivity. For example, a >20:1 ratio was obtained in the presence of the Corey diamine ligand:
    • Asymmetric dihydroxylation under the stoichiometric conditions gave a much higher selectivity. For example, a >20:1 ratio was obtained in the presence of the Corey diamine ligand:. Corey E.J., Jardine P.D., Virgil S., Yuen P.-W., and Connel R.D. J. Am. Chem. Soc. 111 (1989) 9243
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 9243
    • Corey, E.J.1    Jardine, P.D.2    Virgil, S.3    Yuen, P.-W.4    Connel, R.D.5
  • 30
    • 34248647465 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of crude product.
  • 33
    • 34248667164 scopus 로고    scopus 로고
    • Remote diastereomers are referred to as the diastereomers due to the stereocenter(s) present outside a self-contained box(es); see:
  • 36
    • 34248661977 scopus 로고    scopus 로고
    • Mycolactones are known to exhibit intriguing biological properties; see:
  • 38
    • 0034777404 scopus 로고    scopus 로고
    • and references cited therein. We thank Professor P.L.C. Small at the University of Tennessee for performing biological tests
    • Dobos K.M., Small P.L., Deslauriers M., Quinn F.D., and King C.H. Infect. Immun. 69 (2001) 7182 and references cited therein. We thank Professor P.L.C. Small at the University of Tennessee for performing biological tests
    • (2001) Infect. Immun. , vol.69 , pp. 7182
    • Dobos, K.M.1    Small, P.L.2    Deslauriers, M.3    Quinn, F.D.4    King, C.H.5
  • 46
    • 34248632401 scopus 로고    scopus 로고
    • note
    • With use of the C1-carboxylate aldehyde (shown below) for Brown crotylboration, the two steps required for the oxidation of the primary alcohol to the acid could be eliminated. However, the crotylboration gave a 3:1 mixture of the desired product and the δ-lactone.{A figure is presented}
  • 53
    • 0033603829 scopus 로고    scopus 로고
    • There are several modified protocols known for the Negishi coupling reaction. The procedure used here was modified from the Stille coupling protocol reported by Corey:
    • There are several modified protocols known for the Negishi coupling reaction. The procedure used here was modified from the Stille coupling protocol reported by Corey:. Han X., Stoltz B.M., and Corey E.J. J. Am. Chem. Soc. 121 (1999) 7600
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 7600
    • Han, X.1    Stoltz, B.M.2    Corey, E.J.3
  • 54
    • 34248638052 scopus 로고    scopus 로고
    • note
    • To adopt this synthesis for our purpose, it would be necessary to adjust the C12′-OH protecting group, i.e., from the MOM ether to the TBS ether.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.