No abstract

The first total synthesis of the chlorinated resorcylic acid lactone cochliomycin C is achieved starting from the readily available sugar D‐lyxose. The strategy has also lead to the total synthesis of natural resorcylic acid lactones paecilomycin E, paecilomycin F and a synthetic analogue 6‐epi‐cochliomycin C. The key reactions include Ohira–Bestmann alkynylation, ring closing metathesis and regioselective methylation under Mitsunobu conditions.

A facile and convergent approach for the total synthesis of 14-membered resorcylic acid lactone paecilomycin F is described. The synthesis emanates from the readily available inexpensive (+)-diethyl L-tartrate. Mitsunobu etherification, Stille coupling and ring-closing metathesis are key steps in the synthesis.

A Carbohydrate Approach for the First Total Synthesis of Cochliomycin C (I): Stereoselective Total Synthesis of Paecilomycin E, Paecilomycin F and 6'-epi--Cochliomycin C. -Starting from readily available sugar D-lyxose, a unique strategy for the total synthesis of natural resorcylic acid lactones involving an Ohira-Bestmann alkynylation, ring closing metathesis, and regioselective methylation under Mitsunobu conditions as key steps is accomplished. -(MAHANKALI, B.; SRIHARI*, P.; Eur. J. Org. Chem. 2015, 18, 3983-3993, http://dx.