A Concise Synthesis of the Octalactins
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. Holmes
10.1021/ja038353w.s003
https://acs.figshare.com/articles/dataset/A_Concise_Synthesis_of_the_Octalactins/3348652
The 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 PatersonāAldol reaction
for the rapid assembly of the carbonate <b>46</b>, methylenation of <b>46</b> and subsequent Claisen rearrangement
of the corresponding alkenyl-substituted cyclic ketene acetal to provide the core unsaturated medium-ring
lactone <b>47</b>, and the use of enzyme-mediated acetate deprotection in the presence of a medium-ring lactone.
2004-02-25 00:00:00
Concise Synthesis
acetate
presence
Paterson
ketene
Claisen rearrangement
Key steps
sequence
methylenation
acetal
Octalactin
core
assembly
deprotection
material
15 steps
octalactin
lactone
cyclic
carbonate 46
synthesis