254731-57-2Relevant academic research and scientific papers
Oxabicyclo[3.2.1]oct-6-enes as templates for the stereoselective synthesis of polypropionates: Total synthesis of callystatin a and C19-epi-callystatin A
Lautens, Mark,Stammers, Timothy A.
, p. 1993 - 2012 (2007/10/03)
The total synthesis of the polyketide natural product callystatin A and its novel analog C19-epi-callystatin A is described. Our strategy features the use of an enantiomerically pure oxabicyclo[3.2.1]oct-6-ene as a template for the stereocontrolled preparation of the C15-C21 polypropionate region.
Cerium(III) chloride promoted opening of [3.2.1] oxabicycles with methyllithium
Lautens, Mark,De Frutos, Oscar,Stammers, Timothy A.
, p. 8317 - 8321 (2007/10/03)
Previously reported 1-cyclohexylhydroxymethyl-2,4-dimethyl-8-oxabicyclo [3.2.1]octen-3-ols 2 can be ring opened to produce substituted cycloheptenes 3 in a highly regio- and stereoselective reaction using MeLi in the presence of CeCl3. These functionalized cycloheptenes contain an array of five contiguous stereocenters which provide access to polypropionate fragments with 1,3,5-syn,syn methyl groups.
