308350-13-2Relevant academic research and scientific papers
High stereochemical diversity and applications for the synthesis of marine natural products: A library of carbohydrate mimics and polyketide segments
Misske, Andrea M.,Hoffmann, H. Martin R.
, p. 3313 - 3320 (2007/10/03)
We have developed a powerful concept for the rapid assembly of a series of twenty-four homochiral building blocks from simple racemic trans-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one. The series comprises eight stereochemical pentades of anomeric [3.3.1]lactone acetals, eight stereochemical tetrades of anomeric carbohydrate mimics, and eight stereotetrades of acyclic polypropionate units. The utility of these enantiopure materials (average 94% ee) in natural product synthesis is demonstrated and shown to complement the popular aldol method.
