Nitrolaldol reaction of (R)-2,3-cyclohexylideneglyceraldehyde: A simple and stereoselective synthesis of the cytotoxic Pachastrissamine (Jaspine B)

Article abstract of DOI:10.1016/j.tetasy.2010.06.024

(R)-2,3-Cyclohexylideneglyceraldehyde 1 has been found to be a good substrate for nitroaldol reaction both in anhydrous and aqueous conditions. In both cases, the reaction took place with good substrate-controlled anti-selectivity. The major nitroaldol product 2b has been exploited to develop a simple and stereoselective synthesis of jaspine B X. Also, beginning with nitroaldol reaction of 1, this route presents a simple approach for the stereoselective preparation of (anti-anti-5,7)- and (syn-syn-9, 11, 12)-1,2,3,4-alkanetetrols, each possessing three contiguous oxygenated stereocenters.