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Synlett
Volumn , Issue 11, 2008, Pages 1665-1668
Studies on the synthesis of bitungolides A-E: Synthesis of the C(1-C(12) fragment
Author keywords

Allylation; Bitungolide; Dihydroxylation; Evans aldol reaction; Myers alkylation
Indexed keywords

BITUNGOLIDE A; BITUNGOLIDE B; BITUNGOLIDE C; BITUNGOLIDE D; BITUNGOLIDE E; NATURAL PRODUCT;
EID: 48349115139     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078486     Document Type: Article
Times cited : (13)
References (27)
  • 27
    • 48349125749 scopus 로고    scopus 로고
    • Selected Experimental and Spectroscopic Data Compound 1900 A solution of n-BuLi in hexane (1.85 M, 15.8 mL, 29.23 mmol) was added via cannula to a suspension of LiCl (3.94 g, 92.73 mmol) and diisopropylamine (4.4 mL, 32.86 mmol) in THF (50 mL) at -78 °C. The resulting suspension was warmed to 0 °C briefly and then was cooled to -78 °C, an ice-cooled solution of amide, )-18 (3.39 g, 15.33 mmol) in THF (50 mL, followed by a 4 mL rinse) was added via cannula. The mixture was stirred at -78 °C for 1 h, at 0 °C for 15 min and at 23 °C for 5 min. The mixture was cooled to 0 °C, and iodide 17 (3.125 g, 7.33 mmol) was added neat to the reaction via cannula. After being stirred for 18 h at 0 °C, the reaction mixture was treated with half-saturated aq NH4Cl solution (40 mL) and the resulting mixture was extracted with EtOAc 4 × 50 mL, The combined organic extracts were dried over Na2SO4 and concentrate
    • 4 (0.18 mL, 1.54 mmol) and the mixture allowed to stir for 5 min. Subsequently, (-)-sparteine (0.862 g, 3.68 mmol) was added to the yellow slurry. The dark red enolate solution was stirred for 20 min at 0 °C before aldehyde 10 (632 mg, 1.76 mmol)

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.