Enantioselective Syntheses of Pachastrissamine and Jaspine A via Hydroxylactonization of a Chiral Epoxy Ester
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概要
- 論文の詳細を見る
A new enantioselective total synthesis of pachastrissamine (jaspine B) was achieved from a known α,β-unsaturated aldehyde by utilizing Córdova’s asymmetric epoxidation as the chirality-inducing step. The 2,3-cis stereochemistry of pachastrissamine was established via intramolecular epoxide ring opening of a γ,δ-epoxy-α,β-unsaturated ester intermediate coupled with oxy-Michael cyclization. Treatment of pachastrissamine with tetrahydro-2-furanol under acidic conditions led to smooth oxazolidine ring formation, furnishing jaspine A in a high yield.
- 社団法人 日本農芸化学会の論文
- 2010-01-23
著者
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Kuwahara Shigefumi
Laboratory Of Agricultural Chemicals Faculty Of Agriculture Ibaraki University
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Enomoto Masaru
Laboratory Of Applied Bioorganic Chemistry Graduate School Of Agricultural Science Tohoku University
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URANO Hiroyuki
Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku Universi
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Urano Hiroyuki
Laboratory Of Applied Bioorganic Chemistry Graduate School Of Agricultural Science Tohoku University
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