Alkylated Levoglucosan in Organic Synthesis. : A Formal Total Synthesis of Elaiophylin

摘要: Levoglucosan (8) has been found to be a useful material for the synthesis of chiral compounds having five contiguous centers (14). Conversion 8 14 involves two trans-diaxial openings epoxides by nucleophilic reagents. Among 14, 14c was successfully transformed into intermediate 5 total elaiophylin (1). Efficient lactonization carboxylic acid 33 achieved use Yamaguchi's method.