Total synthesis of everninomicin 13,384-1 - Part 3: Synthesis of the DE fragment and completion of the total synthesis

Article abstract of DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

The stereoselective construction of the DE fragment (2) of everninomicin 13,384-1 (1) is reported. From the two possible ways of inserting the DE fragment between the A₁B(A)C and FGHA₂ domains of the natural product, the sequence involving the DEFGHA₂ segment was found to be the most viable. This coupling was followed by attachment of a suitably protected and activated A₁B(A)C fragment which led, after orthoester construction and final deprotection to the targeted everninomicin 13,384-1 (1), completing the total synthesis of this complex naturally occurring substance.