Abstract
Using a carbenoid rearrangement to introduce the conjugated acetylenic framework, a series of triynols has been synthesized in five steps from 1,4-butynediol. Several of the triyne alcohols are known natural products and others are glycosylated analogues. This route avoids the use of terminal diynes as precursors, which can be unstable and/or difficult to prepare. It is therefore procedurally attractive in comparison to more traditional routes such as the Cadiot-Chodkiewicz and Sonogashira coupling reactions.
Key words
polyacetylenes - polyynes - carbohydrates - Fritsch-Buttenberg-Wiechell reaction - carbenoids - natural products
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