The unusual course of the reaction of 3β-acetoxylanost-5-en-7-one with p-toluenesulphonylhydrazine

✍ Scribed by Jacek J. Jagodziński; Rafat R. Siciński

• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 234 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)86755-6

✦ Synopsis

During the attempted preparation of the p-toluenesulphonylhydrazone of enone 2 it has been established that a reductive side reaction occurs -probably brought about by di-imide, arising from the thermal decomposition of p-toluenesulphonylhydrazine. In connection with our studies 1 directed towards the photochemistry of lanostadiene derivatives, we sought an improved route to 3&acetoxylanosta-5,7-diene (3) which would be readily applicable to formation of a hitherto unknown lanostone analogue of vitamin Ds. A four step synthesis of diene 3 was