Total synthesis of cucurbitoside A using a novel fluorous protecting group

The first total synthesis of cucurbitoside A was achieved using a new fluorous N-phenylcarbamoyl (FCar) protecting group. The FCar group was introduced into carbohydrates in high yield and was selectively removed with Bu4NNO2 without damaging other acyl protecting groups. The synthetic intermediates were easily isolated by fluorous solid-phase extraction.