Journal of Organic Chemistry p. 5153 - 5161 (1989)
Update date:2022-08-02
Topics:
Kotsuki, Hiyoshizo
Ushio, Yasuyuki
Kadota, Isao
Ochi, Masamitsu
A general synthetic strategy for constructing seven- and eight-membered cyclic ether derivatives is described.The important feature of this work is a highly stereoselective reduction of bicyclic ketals, i.e., cis-selective reduction with triethylsilane/TiCl4 and trans-selective reduction with diisobutylaluminum hydride (DIBAL).The procedure completed a new and efficient synthesis of isolaurepinnacin and lauthisan skeletons in optically active forms.
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