Amino acid-derived heterocycles as combinatorial library targets: spirocyclic ketal lactones.
The spirocyclic ketal-lactone frameworks of 3 and 4 were designed as novel structures amenable to combinatorial synthesis. The synthesis of representative analogues was developed in solution and on solid support, the scope of effective input materials was determined, and the stability and stereochemistry of the products was evaluated. The spirocycles are obtained in modest overall yields (5-36%) and excellent purities (>72%) and offer a promising motif for combinatorial prospecting libraries.
Trump
Ryan P
RP
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720-1460, USA.
Bartlett
Paul A
PA
D019342:Acetic Acid / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000596:Amino Acids; D007783:Lactones; D019342:Acetic Acid