Synthesis of the Cyclohexane Fragment Peculiar to Enacyloxins: Study of Its Assembly and Protective Groups Removal

Abstract

The enantioselective synthesis of the protected (1S,3R,4S)-3,4-dihydroxycyclohexane-1-carboxylic acid moiety shared among all members of the enacyloxin family has been successfully accomplished. Having obtained this fragment, we devised assembly conditions using models that mimic the enacyloxin acyl chain. Additionally, we assessed conditions for the removal of protective groups, aiming to avoid previously reported detrimental ester shifts.

Key words

total synthesis - natural products - ring-closing metathesis - palladium - carbonylation - kinetic reprotonation

• References

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