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Volumn , Issue 17, 2008, Pages 2651-2654

Total syntheses of diospongins A and B

Author keywords

Diospongin; Epoxide; Rearrangement; Silicon; Total synthesis

Indexed keywords

2,6 DISUBSTITUTED DIHYDROPYRANONE DERIVATIVE; DIOSPONGIN A; DISOPONGIN B; PHTHALIC ACID DIMETHYL ESTER; PLANT EXTRACT; UNCLASSIFIED DRUG;

EID: 55449109711     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083518     Document Type: Article
Times cited : (28)

References (20)
  • 12
    • 55449099499 scopus 로고    scopus 로고
    • To a well-stirred solution of TBS-dithiane 3 (120 mg, 0.51 mmol) in Et2O (2 mL, t-BuLi was added (1.7 M in hexane, 0.43 mL) via syringe at -78 °C. The reaction mixture was stirred for 1 h at -40 °C. Then, a solution of epoxide 5 (1 mmol) in Et2O (1 mL) was added to the reaction mixture at -78 °C. The mixture was allowed to warm to 0 °C over 1 h and then recooled to -78 °C. A solution of epoxide 4 (1.1 mmol) in Et2O-HMPA (90 mg HMPA in 1 mL of Et 2O) was added. The reaction mixture was stirred from -78 to 0 °C overnight, then quenched with sat. aq NH4Cl (1 mL, After dilution of the mixture with Et2O, the organic layer was separated. The aqueous phase was extracted three times with Et2O, and the combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Flash chromatography (hexanes-EtOAc, 30:1) provided
    • +.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.