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Synthesis and Configuration of Some Hydroxymilbemycin Derivatives Including 22,23-Dihydroavermectin B1b Aglycone

✍ Scribed by Bruno Frei; Philip Huxley; Peter Maienfisch; Hari Babu Mereyala; Günther Rist; Anthony C. O'Sullivan


Publisher
John Wiley and Sons
Year
1990
Tongue
German
Weight
878 KB
Volume
73
Category
Article
ISSN
0018-019X

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✦ Synopsis


In toluene as solvent, the azidoalcohol was formed [lza].

HELVETICA CHIMICA ACTA Scheme 1

Vo1. 73 (1990) 1907

Oxidation of the 13a -hydroxy derivatives 15A and 15D with PDC in DMF afforded the ketones 14A and 14D in good yield [6b].


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✍ Thomas L. Shih; Helmut Mrozik; Mark A. Holmes; Bryon H. Arison; George A. Doss; 📂 Article 📅 1992 🏛 Elsevier Science 🌐 French ⚖ 284 KB

Treatment of 4",S-di-G-tert-butyldimethylsilyl(or phenoxyacetyl)-7-0-trimethylsilyl-avenue&n B2a (la,b) with diethylaminosulfur trifluoride (DAST) at 20AC in dichloromethane resulted in net elimination of water to yield 65% of the 23,24-olefin (Za,b), 510% 23-fluoroavermectin derivative (3a,b), and