Total Synthesis of Panaginsene |
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Authors: | Vipin Kumar Singh Prof Tushar Kanti Chakraborty |
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Institution: | Department of Organic Chemistry, Indian Institute of Science, Bengaluru, 560012 India |
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Abstract: | The total synthesis of panaginsene has been accomplished in 11 linear steps starting from methyl 3,3-dimethyl-5-oxocyclopent-1-ene-1-carboxylate. The key steps are a Sharpless asymmetric epoxidation and Ti(III)-mediated reductive epoxide opening-radical cyclization to construct the chiral quaternary carbon stereocenter followed by a very challenging HWE olefination reaction on an 1,3-keto aldehyde and a late stage McMurry olefination using low valent titanium to construct the highly constrained angular tetrasubstituted olefin in a five-membered ring. |
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Keywords: | Conjugate addition Sharpless asymmetric epoxidation Cp2TiCl HWE olefination McMurry olefination |
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