A Total Synthesis of Galbonolide B
Philip J. Parsons
Lewis Pennicott
James Eshelby
Matthias Goessman
Adrian Highton
Peter Hitchcock
10.1021/jo701509r.s006
https://acs.figshare.com/articles/dataset/A_Total_Synthesis_of_Galbonolide_B/2972839
An ester enolate rearrangement/silicon mediated fragmentation cascade was used to convert <b>7</b> and <b>8</b> into the alcohol <b>9</b>.
The alcohol <b>9</b> was converted into the allylic alcohol <b>12</b> and
then to the ester <b>14</b>. A further ester enolate rearrangement
furnished the stereochemical identity of galbonolide B <b>1</b>.
Base mediated macrocyclization of the acetate ester <b>16</b>
followed by base mediated alkylation and acetal deprotection
gave galbonolide B <b>1</b>.
2007-11-23 00:00:00
allylic alcohol 12
acetate ester 16
galbonolide B 1
alcohol 9
ester enolate rearrangement