A synthesis of petrofuran based on the enantioselective reduction of 1- trimethylsilyl-4-alken-1-yn-3-ones

Synlett

Volumn , Issue 4, 1999, Pages 429-431

  Garcia, J ^a   Lopez M ^a   Romeu, J ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Enantioselective reduction; Oxazaborolidines; Petrosia sp.; Polyacetylenes; Sponge metabolites

Indexed keywords

TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; ENANTIOMER; REACTION ANALYSIS; REACTION TIME; REDUCTION; SYNTHESIS;

EID: 0344076150     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-6183     Document Type: Article

References (28)

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13. 2 and 6 under similar conditions for 1 h, 5 was recovered in only 50% yield, but with negligible lost of e.e. In this connection, it is worth noting that when only 0.2 mmols of 6 were used in the reduction step, the reaction became slower and chemical yield considerably dropped.
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23. 1H-NMR spectrum of the crude product).
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25. 2O before use to obtain good yields.
26. ++18, 10%), 226 (100%).
27. Stereoisomeric ratios were obtained by HPLC analysis (Spherisorb S3W column, hexane/AcOEt 95:5) of the corresponding Mosher diesters.
28. Spectral data of 3 fully agree with those reported in ref. 5.