Stereoselective Construction of Tetra-Substituted Tetrahydrofuran Compounds from Benzylic Hemiacetal in the Presence of H2and a Pd Catalyst: Stereoselective Synthesis of a Stereoisomer of (−)-Virgatusin and Its Antimicrobiological Activity
Bioscience Biotechnology and Biochemistry2008Vol. 72(1), pp. 197–203
Tomofumi Nakato, Ryosuke Tago, Koichi Akiyama, Masafumi Maruyama, Takuya Sugahara, Taro Kishida, Satoshi Yamauchi
Abstract
Tetra-substituted tetrahydrofuran compounds were stereoselectively prepared from benzylic hemiacetal in the neutral condition by employing the simple reagent, H(2), and a Pd catalyst. The stereoselective conversion of benzylic hemiacetal to two different stereoisomers of the tetrasubstituted tetrahydrofuran compound was observed. One of these tetrahydrofuran compounds was converted to the virgatusin stereoisomer to estimate its antimicrobiological activity.
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