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Communication | Special issue | Vol 30, No. 1, 1990, pp.321-324
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S54
Stereocontrolled Synthesis of C18-C24 Fragments of Isolasalocid A and Lasalocid A. An application of the Acid Assisted Synthesis of Functionalized Tetrahydrofurans and Tetrahydropyrans

Kiyoshi Horita, Ichio Noda, Kazuhiro Tanaka, Tamaki Miura, and Osamu Yonemitsu*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan


The allyl alcohol (9) derived from D-glucose was easily cyclized by acid treatment and then converted to the C18-C24 fragment (13) of isolasalocid A (5). Similarly, the allyl alcohol (15) derived from ethyl L-lactane was converted to the C18-C24 fragment (20) of lasalocid A (6) via the tetrahydropyran derivative (16), which was kinetically formed by a chelation-controlled reaction.