Synthesis of E-deoxypukalide, and its biomimetic conversion into deoxypseudopterolide by photochemical ring contraction involving a 1,3-allylic shift |
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Authors: | Zhi Yang |
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Institution: | School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK |
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Abstract: | Irradiation of a solution of synthetic Z-deoxypukalide 10 in acetonitrile (Pyrex; 400 W Hg lamp) resulted in isomerisation, leading to E-deoxypukalide 12, which was isolated recently from the octocoral Leptogorgia spp. Further irradiation of 12, or prolonged irradiation of 10, then gave the ring-contracted product, deoxypseudopterolide 1 (>90%) found in octocorals of the genera Pseudopterogorgia and Leptogorgia. The contraction of the 14-membered rings in 10 and 12 to the 12-membered ring as 1, occurs by way of photochemical 1,3]-sigmatropic rearrangement. |
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Keywords: | Photochemical ring contraction 1 3-Allylic shift [1 3] Sigmatropic rearrangement E-Deoxypukalide Deoxypseudopterolide Octocorals |
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