ja038353w_si_003.cif (13.47 kB)
A Concise Synthesis of the Octalactins
dataset
posted on 2004-02-25, 00:00 authored by Paul T. O'Sullivan, Wilm Buhr, Mary Ann M. Fuhry, Justin R. Harrison, John E. Davies, Neil Feeder, David R. Marshall, Jonathan W. Burton, Andrew B. HolmesThe total synthesis of octalactins A and B has been achieved in 15 steps (longest linear sequence)
and 10% overall yield from commercially available materials. Key steps include the Paterson−Aldol reaction
for the rapid assembly of the carbonate 46, methylenation of 46 and subsequent Claisen rearrangement
of the corresponding alkenyl-substituted cyclic ketene acetal to provide the core unsaturated medium-ring
lactone 47, and the use of enzyme-mediated acetate deprotection in the presence of a medium-ring lactone.
