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Volumn 13, Issue 19, 2011, Pages 5398-5401

Total synthesis of Oxazolomycin a

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; DIFFUSOMYCIN; INDIUM; OXAZOLE DERIVATIVE; SPIRO COMPOUND;

EID: 80054763490     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202306d     Document Type: Article
Times cited : (49)

References (59)
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    • For a review
    • For a review
  • 11
    • 80054747356 scopus 로고    scopus 로고
    • For reviews
    • For reviews
  • 34
    • 61449241709 scopus 로고    scopus 로고
    • The early stages of the work were presented at the 17th International Conference on Organic Synthesis
    • (ICOS-17), Daejeon, Korea, June 22-27, 2008
    • The early stages of the work were presented at the 17th International Conference on Organic Synthesis (ICOS-17) (Daejeon, Korea, June 22-27, 2008). Hatakeyama, S. Pure Appl. Chem. 2009, 81, 217.
    • (2009) Pure Appl. Chem , vol.81 , pp. 217
    • Hatakeyama, S.1
  • 37
    • 80054741642 scopus 로고    scopus 로고
    • Highly improved in total yield and number of steps compared with the previous route12b (24% in 14 steps versus 15% in 17 steps)
    • Highly improved in total yield and number of steps compared with the previous route12b (24% in 14 steps versus 15% in 17 steps).
  • 38
    • 84856526246 scopus 로고    scopus 로고
    • 2O) did not undergo methylation
    • 2O) did not undergo methylation.
  • 41
    • 0035953035 scopus 로고    scopus 로고
    • Sawada's protocol was modified using odorless dodecanethiol in place of malodorous ethanethiol according to the technique developed by Node
    • Sawada's protocol was modified using odorless dodecanethiol in place of malodorous ethanethiol according to the technique developed by Node et al. Sawada, D.; Ito, Y. Tetrahedron Lett. 2001, 42, 2501.
    • (2001) Tetrahedron Lett , vol.42 , pp. 2501
    • Sawada, D.1    Ito, Y.2
  • 43
    • 80054727101 scopus 로고    scopus 로고
    • Previously, compound 4 was prepared from propargyl alcohol in 18% yield (9 steps). See the Supporting Information of ref 12b
    • Previously, compound 4 was prepared from propargyl alcohol in 18% yield (9 steps). See the Supporting Information of ref 12b.
  • 50
    • 84856524737 scopus 로고    scopus 로고
    • Isobutyryl chloride was not effective for the cyclocondensation reaction with 20, and the desired β-lactone was not obtained at all
    • Isobutyryl chloride was not effective for the cyclocondensation reaction with 20, and the desired β-lactone was not obtained at all.
  • 51
    • 84856549370 scopus 로고    scopus 로고
    • The cyclocondensation reaction with the E-isomer of 20 gave the corresponding β-lactone in excellent enantio- and diastereoselectivity (97% ee, >99% de) in 82% yield. The geometrically isomeric left-hand segments of oxazolomycins B and C were stereoselectively synthesized from this β-lactone. These syntheses will be reported in due course
    • The cyclocondensation reaction with the E-isomer of 20 gave the corresponding β-lactone in excellent enantio- and diastereoselectivity (97% ee, >99% de) in 82% yield. The geometrically isomeric left-hand segments of oxazolomycins B and C were stereoselectively synthesized from this β-lactone. These syntheses will be reported in due course.
  • 54
    • 84856549371 scopus 로고    scopus 로고
    • 12b (29% in 14 steps versus 12% in 17 steps)
    • 12b (29% in 14 steps versus 12% in 17 steps).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.