&&g& When treated with a reagent prepared from equimolar quantities of methyllithium and copper iodide, 7,21-d&O-TMS baf%mycin A2 3 undergoes ring expansion to give the 1 I-membered lactone homolog 5 in nearly quantitative yield. Acid hydrolysis gives iso-bafilomycin Al. Ring contraction to the orig
Ring Expansion in the Benzofuran Series
β Scribed by Dr. Bernard Libis; Dr. Ernst Habicht
- Publisher
- John Wiley and Sons
- Year
- 1971
- Tongue
- English
- Weight
- 116 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0044-8249
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β¦ Synopsis
ed on GC-MS of the original acid fluoroheptyl ester mixture['] at the retention time of ester (1 f).
In addition, two stereoisomeric C,,-steroid carboxylic acids were identified. Although structural proof is not complete, present results suggest that they are 5a-(Ig) and 5 B-cholanic acids.
The significance of this work is that these are the first polycyclic naphthenic carboxylic acids ever reported in petroleum as individual compounds; and on top of this they possess biological precursor hydrocarbon skeletons and, therefore, are geochemically significant. Animal bile acids are considered to be the most likely precursors.
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