On the front cover of this issue is work from Debendra Mohapatra at the Indian Institute of Chemical Technology, together with colleagues at Hyderabad University and King Saud University on the ring-closing metathesis based synthesis of the macrolactone core of amphidinolactone A.
The convergent synthesis achieved the macrolactone core in 32% yield and demonstrated the steric hinderance resulting from protecting groups in the RCM reaction. PMB (p-methoxybenzyl ether) protecting groups on the macrolactonization precursor prevented the RCM reaction from proceeding, but simple de-protection to the subsequent diol achieved the 13-membered lactone ring system present in amphidinolactone A in 76% yield. Further work to incorporate the the RCM reaction into the total synthesis of amphidinolactone A is ongoing.
Ring-closing metathesis (RCM) based synthesis of the macrolactone core of amphidinolactone A
Debendra K. Mohapatra, Manas R. Pattanayak, Pragna P. Das, Tapas R. Pradhan and J. S. Yadav
Org. Biomol. Chem., 2011,
DOI: 10.1039/C1OB05335C
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