Total synthesis and absolute configuration of liverwort diterpenes, (-)-13(15)E,16E-3beta,4beta-epoxy-18-hydroxysphenoloba-13(15),16-diene and (-)-13(15)Z,16E-3beta,4beta-Epoxy-18-hydroxysphenoloba-13(15),16-diene,by use of the ring closing metathesis reaction applied to seven-membered carbocycles with a trisubstituted double bond |
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Authors: | Nakashima Katsuyuki Inoue Kosuke Sono Masakazu Tori Motoo |
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Institution: | Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan. |
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Abstract: | Seven-membered cyclic compounds possessing trisubstituted double bonds have been effectively constructed employing the Grubbs catalyst to effect olefin metathesis. The keto ester does not undergo cyclization; however, alcohols protected by the silyl groups smoothly cyclized into seven-membered compounds. The product was successfully converted to (-)-13(15)E,16E-3beta,4beta-epoxy-18-hydroxysphenoloba-13(15),16-diene and (-)-13(15)Z,16E-3beta,4beta-epoxy-18-hydroxysphenoloba-13(15),16-diene, liverwort diterpenes isolated from Anastrophyllum auritum to establish the absolute configuration. |
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