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First stereoselective total synthesis of Neocosmosin A: a facile approach
Authors:Soma Shekar Dachavaram  Kondbarao Balasaheb KalyankarSaibal Das
Institution:Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India
Abstract:First stereoselective concise synthesis of Neocosmosin A, with in vitro binding affinity for human opioid and cannabinoid receptors, has been reported using readily available starting materials such as methylacetoacetate, cyclohexanone, and homoallyl alcohol involved in the key transformations. There are three fragments involved in the synthesis of target molecule, bearing acid functionality, (R)-pent-4-en-2-ol, and Weinreb amide which are synthesized in four, eight, and three steps, respectively. Then the fragments were coupled in four steps to yield the target molecule in an overall yield of 28.6%.
Keywords:Neocosmosin A  Resorcylic acid lactones  Total synthesis
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