Stereoselective synthesis of stiophilate and sitophilure

Tetrahedron Asymmetry

Volumn 7, Issue 12, 1996, Pages 3479-3484

  Razkin, Jesús ^a   González, Alberto ^a   Gil, Pilar ^a  

^a PUBLIC UNIVERSITY OF NAVARRE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PHEROMONE;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030561212     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00455-7     Document Type: Article

References (34)

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32. 24. Higher yield of keto ester 2 (89%) (which would lead to 48% overall yield of sitophilate) was obtained when an excess of methyl 3-oxopentanoate instead of 3-pentanol was used. However, the advantage of using an excess of alcohol, besides its lower price, is that it is easier to recover.
33. 25. Whenever -30°C was needed, the reaction mixture was kept in a freezer, instead of using a cryogenic bath.
34. 1H-NMR: δ 0.80 (t, J=7.1 Hz, 3H), 0.92-0.97 (2d, J=7 Hz, 3H), 1.20-1.75 (m, 8H, 6H from THP), 2.30-2.50 (m, 1H), 3.20-3.40 (m, 1H from THP), 3.55-3.92 (m, 2H, 1H from THP), 4.40-4.60 (m, 1H from THP), 9.62 (d, J=0.7 Hz, 1H).