The use of a mannitol-derived fused oxacycle as a combinatorial scaffold.
An efficient and high-yielding solid-phase synthesis of a small library of compounds containing a cis-fused pyranofuran structural motive is described. With use of the cheap and readily available D-(+)-mannitol, a highly functionalized sugar template was synthesized and immobilized on a solid support via an olefinic linker. Modification of this two-point molecular scaffold and subsequent ring-closing metathesis/cleavage gave access to a series of functionalized conformationally constrained fused oxacycles.
Timmer
Mattie S M
MS
Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Verdoes
Martijn
M
Sliedregt
Leo A J M
LA
van der Marel
Gijsbert A
GA
van Boom
Jacques H
JH
Overkleeft
Herman S
HS
D002625:Chemistry, Organic / Q000379:methods; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003500:Cyclization; D008353:Mannitol / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D010080:Oxazoles; D008353:Mannitol