Synthesis of substituted butenolides by the ring closing metathesis of two electron deficient olefins: a general route to the natural products of paraconic acids class

Tetrahedron Letters

Volumn 48, Issue 11, 2007, Pages 2021-2024

  Selvakumar, N ^a   Kalyan Kumar, P ^a   Chandra Shekar Reddy, K ^a   Chandra Chary, B ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

Author keywords

Baylis Hillman reaction; Ring closing metathesis

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALKENE DERIVATIVE; BUTENOLIDE; GAMMA BUTYROLACTONE DERIVATIVE; LEWIS ACID; PARACONIC ACID DERIVATIVE; PHASEOLINIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; ELECTRON; METHODOLOGY; RING CLOSING METATHESIS; SUBSTITUTION REACTION;

EID: 33846925525     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.053     Document Type: Article

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24. General experimental procedure for RCM: A two-neck flask equipped with a condenser was flame dried in vacuo and charged successively with a solution of the diene (0.01 M) in dry DCM followed by titanium tetraisopropoxide (10 mol %) under argon. To this solution was added dropwise a 0.01 M solution of catalyst 12 (10 mol %) in dry DCM over 12 h at reflux using a syringe pump. The mixture was stirred at reflux for a further 24 h. The reaction mixture was allowed to cool and then washed with water, brine and dried. The solvent was removed in vacuo and the residue was purified by silica gel chromatography to separate the desired cyclisation product from the recovered starting material.
25. The starting dienes for entries 1-6 were prepared from the corresponding acrylates and appropriate aldehydes using Baylis-Hillman reactions followed by acryloylation. Following the same sequence, the dienes in entries 7 and 8 were prepared from methyl vinyl ketone and acrylonitrile, respectively.
26. -1.
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