title: Use of benzofuran for concomitant protection of aldehyde and phenol groups in the preparation of mycophenolic acid analogues.
abstract: 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.
authors.affiliation: Gilead Sciences, 333 Lakeside Drive, Foster City, California 94404, USA. mfardis@gilead.com
authors.forename: Maria
authors.initials: M
authors.lastname: Fardis
authors.forename: Michael
authors.initials: M
authors.lastname: Mertzman
authors.forename: William
authors.initials: W
authors.lastname: Thomas
authors.forename: Thorsten
authors.initials: T
authors.lastname: Kirschberg
authors.forename: Nicole
authors.initials: N
authors.lastname: Collins
authors.forename: Richard
authors.initials: R
authors.lastname: Polniaszek
authors.forename: William J
authors.initials: WJ
authors.lastname: Watkins
mesh_terms: 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
chemical_list: D000447:Aldehydes; D001572:Benzofurans; D010636:Phenols; D009173:Mycophenolic Acid; C105430:benzofuran