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Volumn 324, Issue 5924, 2009, Pages 238-241

Total synthesis of (+)-11/11'-Dideoxyverticillin A

Author keywords

[No Author keywords available]

Indexed keywords

11,11' DIDEOXYVERTICILLIN A; ALKALOID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 64849113664     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1170777     Document Type: Article
Times cited : (288)

References (37)
  • 6
    • 64849110380 scopus 로고    scopus 로고
    • For other representative syntheses of epidithiodiketo-piperazines, see (35) and references cited therein
    • For other representative syntheses of epidithiodiketo-piperazines, see (35) and references cited therein.
  • 7
    • 64849103733 scopus 로고    scopus 로고
    • For a recent total synthesis of a sulfur containing diketopiperazine, see 36
    • For a recent total synthesis of a sulfur containing diketopiperazine, see (36).
  • 15
    • 64849093641 scopus 로고    scopus 로고
    • Sensitivity of diketopiperazine to epimerization at the tryptophan-derived Ca-methine is highlighted by isolation of the corresponding diastereomer of 12 in 11% yield
    • Sensitivity of diketopiperazine to epimerization at the tryptophan-derived Ca-methine is highlighted by isolation of the corresponding diastereomer of 12 in 11% yield.
  • 16
    • 64849096789 scopus 로고    scopus 로고
    • The major isolable side product is the C3-reduction product. Although the use of tetrahydrofuran (THF) as solvent provided a higher yield of dimer (+)-13 (52%) on <1 g scale, the yields of larger scale reactions (>1 g scale) in THF were lower (40%).
    • The major isolable side product is the C3-reduction product. Although the use of tetrahydrofuran (THF) as solvent provided a higher yield of dimer (+)-13 (52%) on <1 g scale, the yields of larger scale reactions (>1 g scale) in THF were lower (40%).
  • 17
  • 22
    • 64849104478 scopus 로고    scopus 로고
    • All attempts at the conversion of tetraene 26 to 1 based on the chemistry developed (fig. S5) in the synthesis of 23 failed, highlighting the additional challenges of the dimeric series.
    • All attempts at the conversion of tetraene 26 to 1 based on the chemistry developed (fig. S5) in the synthesis of 23 failed, highlighting the additional challenges of the dimeric series.
  • 26
    • 64849086467 scopus 로고    scopus 로고
    • In addition to the desired, 11S,11'S,15S, 15'S)-18, the corresponding (11R,11'S,15R,15'S)-18a and (11R,11'R,15R,15'R)-18b diastereomers were also isolated 18:18a:18b, 25:7:1, Exposure of any diastereomer to the reaction conditions does not result in equilibration
    • In addition to the desired (+)-(11S,11'S,15S, 15'S)-18, the corresponding (11R,11'S,15R,15'S)-18a and (11R,11'R,15R,15'R)-18b diastereomers were also isolated (18:18a:18b, 25:7:1). Exposure of any diastereomer to the reaction conditions does not result in equilibration.
  • 27
    • 64849104654 scopus 로고    scopus 로고
    • The expected 1,3-oxazolidine-2-thione (20) was observed in the product mixture.
    • The expected 1,3-oxazolidine-2-thione (20) was observed in the product mixture.
  • 37
    • 64849083100 scopus 로고    scopus 로고
    • M.M. is an Alfred P. Sloan Research Fellow and a Beckman Young Investigator. J.K. and J.A.A. acknowledge predoctoral (National Defense Science and Engineering Graduate) and postdoctoral [Fonds québécois de la recherche sur la nature et les technologies (FQRNT, fellowships, respectively. We thank P. Müller for assistance with x-ray structures of, )-1 and, )-14. We acknowledge generous support from Amgen, AstraZeneca, Boehringer Ingelheim, GlaxoSmithKline, Merck, and Lilly. Structural parameters for and, )-14 are freely available from the Cambridge Crystallographic Data Centre under CCDC-719219 and CCDC-719218, respectively
    • M.M. is an Alfred P. Sloan Research Fellow and a Beckman Young Investigator. J.K. and J.A.A. acknowledge predoctoral (National Defense Science and Engineering Graduate) and postdoctoral [Fonds québécois de la recherche sur la nature et les technologies (FQRNT)] fellowships, respectively. We thank P. Müller for assistance with x-ray structures of (+)-1 and (+)-14. We acknowledge generous support from Amgen, AstraZeneca, Boehringer Ingelheim, GlaxoSmithKline, Merck, and Lilly. Structural parameters for and (+)-14 are freely available from the Cambridge Crystallographic Data Centre under CCDC-719219 and CCDC-719218, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.