Synthesis of 4-Alkyl-4-alkoxybutenolides Having Unsaturated Side Chains via Chromium Carbene Complex Photochemistry: (+)-Cerulenin |
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Authors: | Kedar Tracey E Miller Michael W Hegedus Louis S |
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Institution: | Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523. |
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Abstract: | The photochemical reaction between optically active ene carbamates and chromium alkoxycarbene complexes containing unsaturated aliphatic side chains was further developed. Although remote olefinic groups, including conjugated dienes, were tolerated, a homoallylic side chain underwent intramolecular reaction to give a strained cyclobutanone. (+)-Cerulenin was synthesized utilizing the photochemical reaction of an alkynylcarbene complex with an optically active ene carbamate and the bis(pi-crotyl)nickel halide alkylation of a vinyl bromide as key steps. |
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