Use of benzofuran for concomitant protection of aldehyde and phenol groups in the preparation of mycophenolic acid analogues.
The use of a benzofuran to mask phenol and arylacetaldehyde moieties simultaneously in the synthesis of analogues of mycophenolic acid (MPA) was explored. Benzofuran 4 provided a stable and easily handled intermediate for the preparation of unnatural derivatives at the C-6 position of MPA. Preparation of the highly potent 6-ethyl MPA analogue 2 was accomplished via aldehyde 2c through this facile route with high-yielding steps and crystalline intermediates.
Fardis
Maria
M
Gilead Sciences, 333 Lakeside Drive, Foster City, California 94404, USA. mfardis@gilead.com
Mertzman
Michael
M
Thomas
William
W
Kirschberg
Thorsten
T
Collins
Nicole
N
Polniaszek
Richard
R
Watkins
William J
WJ
D000447:Aldehydes / Q000737:chemistry*; D001572:Benzofurans / Q000737:chemistry*; D015394:Molecular Structure; D009173:Mycophenolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D001572:Benzofurans; D010636:Phenols; D009173:Mycophenolic Acid; C105430:benzofuran