Synthesis of key intermediates for a concise and convergent approach to the marine natural product eleutherobin

Tetrahedron Letters

Volumn 40, Issue 52, 1999, Pages 9321-9324

  Baron, Anne ^a,b   Caprio, Vittorio ^a   Mann, John ^a,b  

^a UNIVERSITY OF READING   (United Kingdom)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ALPHA PHELLANDRENE; ELEUTHEROBIN; FURAN DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033601389     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01956-5     Document Type: Article

References (16)

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7. 15 and purified to afford compound D as a yellow oil (yield:47%).
8. de Almeida Barbosa, L-C.; Mann, J. Synthesis 1996, 31.
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11. 4Cl (120ml). The combined aqueous phases were further extracted with ethyl acetate (2x120ml) and the organic extracts were dried over magnesium sulfate. Solvent was removed under reduced pressure and the resulting brown oil used for the next step without further purification. The crude dibromoadduct 5 was dissolved in saturated methanolic ammonium chloride (250ml) and Zn/Cu couple (26.5g) added portionwise at room temperature. The reaction mixture was stirred 5h at room temperature. After filtration of Zn/Cu couple, ethyl acetate (120ml) and an aqueous saturated solution of NaCl (100ml) were added to the filtrate. After filtration the 2 layers were separated. The aqueous phase was further extracted with ethyl acetate (4x120ml) and the combined organic extracts dried over magnesium sulphate. Solvent was removed under reduced pressure to give 22g of crude product. 6 was then purified by column chromatography on silica gel (petroleum ether/ethyl acetate: 9/1) to yield 3.3g of pure ketone as an orange oil (yield:37%).
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