Synthetic studies on psiguadial B: Construction of bicyclo[4.3.1]decane skeleton via double cyclization reaction of alkyne dicobalt complex |
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Authors: | Masahiko Kinebuchi Ryohei Uematsu Keiji Tanino |
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Institution: | 1. Graduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo 060-0810, Japan;2. Watarase Research Center, Kyorin Pharmaceutical Co., Ltd., Nogi 2399-1, Nogi-machi, Shimotsuga-gun, Tochigi 329-0114, Japan;3. Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan |
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Abstract: | A new method for constructing the polycyclic skeleton of psiguadial B (1), a meroterpenoid isolated from an evergreen shrub of Myrtaceae, was developed. The terpenoid substructure of 1 was constructed on the basis of a cascade double cyclization reaction of an alkyne dicobalt complex, which afforded the bicyclo4.3.1]decane derivative having a benzyl group with the correct configuration. The substituted aromatic ring was introduced to the bridgehead position of the intermediate, and bromination under radical conditions followed by intramolecular cyclization reaction resulted in formation of the benzopyran moiety in a stereoselective manner. |
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Keywords: | Psiguadial Total synthesis Alkyne cobalt complex Cyclization reaction Maleic anhydride |
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