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Volumn 53, Issue 9, 2012, Pages 1186-1189

Total synthesis of stagonolide B

Author keywords

Asymmetric allylation; Cross metathesis; Enzymatic hydrocynation; Macrolactonization; Small ring macrolide

Indexed keywords

CYANOHYDRIN; HYDROXYNITRILE LYASE; NATURAL PRODUCT; STAGONOLIDE B; UNCLASSIFIED DRUG;

EID: 84856232177     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.12.119     Document Type: Article
Times cited : (17)

References (37)
  • 13
    • 77954616757 scopus 로고    scopus 로고
    • For total synthesis of stagonolides and related molecules from other groups see
    • For total synthesis of stagonolides and related molecules from other groups see: P. Srihari, G. Maheswara Rao, R. Srinivasa Rao, and J.S. Yadav Synthesis 2010 2407
    • (2010) Synthesis , pp. 2407
    • Srihari, P.1    Maheswara Rao, G.2    Srinivasa Rao, R.3    Yadav, J.S.4
  • 32
    • 67651087368 scopus 로고    scopus 로고
    • 4). Evaporation of the solvent yielded the crude cyanohydrin which was purified by chromatography. Preparation of HCN in DIPE: NaCN (10 g) and citric acid (0.1 g) were dissolved in water (100 mL). The solution was cooled in an ice/water bath and extracted with DIPE (50 mL), while acidifying with 33% HCl until pH 5.5. The water layer, which contained a suspension of NaCl, was extracted twice with DIPE (25 mL). The combined DIPE layers were stored in a dark bottle. The above procedure must be performed in a well ventilated fume hood with proper glass ware and hand wares (gloves).
    • (2009) Tetrahedron: Asymmetry , vol.20 , pp. 1526-1530
    • Bhunya, R.1    Mahapatra, T.2    Nanda, S.3
  • 34
    • 0034734340 scopus 로고    scopus 로고
    • Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc., 2000, 122, 8168. (E)-3-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy) butyl)-2,2-dimethyl-1,3-dioxolan-4-yl) acrylaldehyde (compound 3): A flame-dried round-bottom flask was charged with olefin 4 (2.5 g 5.7 mmol), freshly distilled acrolein (0.578 ml, 8.66 mmol) and dicholoromethane (25 ml). Hoveyda-Grubbs catalyst (HG-II, 5 mol %) was subsequently added as a solid, producing a light green solution which was refluxed for 6 h. The mixture was then concentrated in vacuo to a dark brown oil. Purification of this residue on silica gel by flash chromatography (pet ether/ethyl acetate: 1/10) affords aldehyde 3 as a yellow oil with 85% yield.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8168
    • Garber, S.B.1    Kingsbury, J.S.2    Gray, B.L.3    Hoveyda, A.H.4
  • 35
    • 20444479416 scopus 로고    scopus 로고
    • 4 and filtered through celite. The crude mixture was purified by flash chromatography (pet ether/ethyl acetate: 5:1) afforded the compound 11 with 76% yield. Formation of a minor diastereomer was indicated in TLC and was separated by chromatography (de = 19:1).
    • (2005) Org. Lett. , vol.7 , pp. 2149
    • Keck, G.E.1    Truong, A.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.