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Volumn 10, Issue 18, 2008, Pages 4125-4128

Total synthesis of the immunosuppressants myriocin and 2-epi-myriocin

Author keywords

[No Author keywords available]

Indexed keywords

2 EPI MYRIOCIN; 2-EPI-MYRIOCIN; IMMUNOSUPPRESSIVE AGENT; MONOUNSATURATED FATTY ACID;

EID: 55949114981     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801709c     Document Type: Article
Times cited : (33)

References (44)
  • 9
    • 33747172279 scopus 로고    scopus 로고
    • For a useful review of synthetic approaches to serine palmitoyl transferase inhibitors, see
    • For a useful review of synthetic approaches to serine palmitoyl transferase inhibitors, see: Byun, H. S.; Lu, X.; Bittman, R. Synthesis 2006, 2447-2474.
    • (2006) Synthesis , pp. 2447-2474
    • Byun, H.S.1    Lu, X.2    Bittman, R.3
  • 12
    • 2142819132 scopus 로고
    • For a synthesis of anhydromyriocin using an essentially nonselective Strecker reaction, see
    • (c) For a synthesis of anhydromyriocin using an essentially nonselective Strecker reaction, see: Just, G.; Fayette, D. R. Tetrahedron Lett. 1980, 21, 3219-3222.
    • (1980) Tetrahedron Lett , vol.21 , pp. 3219-3222
    • Just, G.1    Fayette, D.R.2
  • 25
    • 0344104899 scopus 로고
    • For related approaches to quaternary vinylglycines from dehydroamino acids, see: a
    • For related approaches to quaternary vinylglycines from dehydroamino acids, see: (a) Seebach, D.; Buerger, H. M.; Schickli, C. P. Liebigs. Ann. Chem. 1991, 669-684.
    • (1991) Liebigs. Ann. Chem , pp. 669-684
    • Seebach, D.1    Buerger, H.M.2    Schickli, C.P.3
  • 27
    • 61349149612 scopus 로고    scopus 로고
    • 2 was inferred to be of 95:5 dr, by reductive cyclization of the ester and comparison (90% ee) to racemic oxazolidinone. See ref 16
    • 2 was inferred to be of 95:5 dr, by reductive cyclization of the ester and comparison (90% ee) to racemic oxazolidinone. See ref 16.
  • 28
    • 61349166177 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 32
    • 0037038993 scopus 로고    scopus 로고
    • For reviews of the Julia-Kocienski olefination, see: a
    • For reviews of the Julia-Kocienski olefination, see: (a) Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563-2585.
    • (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 2563-2585
    • Blakemore, P.R.1
  • 37
    • 29044436176 scopus 로고    scopus 로고
    • (66:34 dr): Trost, B. M.; Jiang, C.; Hammer, K. Synthesis 2005, 3335-3345.
    • (c) (66:34 dr): Trost, B. M.; Jiang, C.; Hammer, K. Synthesis 2005, 3335-3345.
  • 41
    • 0035852114 scopus 로고    scopus 로고
    • For dihydroxylation of a quaternary vinylglycine bearing a chiral secondary allylic acetate at the other olefin terminus 70:30 dr, see: Trost, B. M, Lee, C. J. Am. Chem. Soc. 2001, 123, 12191-12201
    • For dihydroxylation of a quaternary vinylglycine bearing a chiral secondary allylic acetate at the other olefin terminus (70:30 dr), see: Trost, B. M.; Lee, C. J. Am. Chem. Soc. 2001, 123, 12191-12201.
  • 44
    • 61349122963 scopus 로고    scopus 로고
    • 1: 16 linear steps from 4, compared with the shortest previous stereoselective route of 16 steps from (Z)-but-2-ene-1,4-diol (ref 12). 7: 11 linear steps to 7 (isolated as 11) from 4, compared with 16 steps to 7 from 2-deoxy-D-glucose (ref 20).
    • 1: 16 linear steps from 4, compared with the shortest previous stereoselective route of 16 steps from (Z)-but-2-ene-1,4-diol (ref 12). 7: 11 linear steps to 7 (isolated as 11) from 4, compared with 16 steps to 7 from 2-deoxy-D-glucose (ref 20).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.