Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
CESIUM FLUORIDE-MEDIATED CLAISEN REARRANGEMENT OF ARYL PROPARGYL ETHER AND ITS APPLICATION TO THE SYNTHESIS OF CHELERYTHRINE
Hisashi ISHIITsutomu ISHIKAWASunao TAKEDASatoshi UEKIMasahiro SUZUKITakashi HARAYAMA
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1990 Volume 38 Issue 6 Pages 1775-1777

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Abstract

In the presence of cesium fluoride, the Claisen rearrangement of aryl propargyl ethers selectively provided 2-methylbenzofurans, which was successively treated with osmium tetroxide, periodic acid and 5% sodium hydroxide to give salicylaldehydes in good yields. The method was used to synthesize chelerythrine (2) via the common intermediate (8) prepared by the two routes as shown in Chart 3.

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© The Pharmaceutical Society of Japan
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