A concise/catalytic approach for the construction of the C14-C28 fragment of eribulin

A simple approach for the synthesis of the C14-C28 fragment of eribulin has been developed by employing a one-pot gold-catalyzed alkynol cyclization/Kishi reduction to construct the 1,5-cis-tetrahydropyran unit and a cross-metathesis/Sharpless asymmetric dihydroxylation-cycloetherification to install the 1,4-trans-tetrahydrofuran ring. Use of easily accessible building blocks, ease of operation and catalytic transformations as key reactions for the construction of THF/THP units highlight the current approach.

Automated summary

A simple approach for synthesizing the C14-C28 fragment of eribulin has been developed by utilizing one-pot gold-catalyzed alkynol cyclization/Kishi reduction and cross-metathesis/Sharpless asymmetric dihydroxylation-cycloetherification reactions. The use of easily accessible building blocks and catalytic transformations highlights the efficiency of the method in constructing the THF/THP units for eribulin synthesis.