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Paper | Special issue | Vol 76, No. 1, 2008, pp.257-265
Published online, 28th December, 2007
DOI: 10.3987/COM-07-S(N)3
Studies on Synthesis of OSW-1 Analogue with Thiazole Ring at Side Chain Employing Wittig Rearrangement

Masayoshi Tsubuki,* Sohichiro Matsuo, and Toshio Honda*

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa, Tokyo 142-8501, Japan


OSW-1 analogue with thiazole at the side chain was synthesized employing a tandem Williamson etherification - [2,3]-Wittig rearrangement, which provided a one-pot producer for the formation of (20S)-22-hydroxy steroids 6 and 7 from the known allylic alcohol 4 and 2-bromomethylthiazole as a key step. Glycosylation of steroid aglycone 17 with donors was investigated under various conditions.