154459-12-8

Upstream product

• 137238-71-2 (4R)-3-[2-(Phenylmethoxy)acetyl]-4-(phenylmethyl)oxazolidin-2-one 
• 19810-31-2 Benzyloxyacetyl chloride 
• 154459-11-7 <3(2R,3S,4E),4R>-4-benzyl-3-(2-benzyloxy-3-hydroxyhex-4-enoyl)oxazolidin-2-one 

Downstream Products

• 154568-63-5 (2S,3S)-1-tert-butyldiphenylsiloxyhex-4-ene-2,3-diol 
• 154568-62-4 (4S,5S)-5-benzyloxy-6-tert-butyldiphenylsiloxyhex-2-en-3-ol 

Relevant academic research and scientific papers

Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

The efficient synthesis of the C(19)-C(26) subunit of amphidinolide B(1) and B(2) has been completed using a boron-mediated aldol reaction. The synthesis of the C(19)-C(26) subunit of amphidinolide B(3) has also been accomplished through an unexpected anti aldol reaction using a titanium-mediated process. In addition, the first reported examples of a stereochemical discrepancy between the Evans' boron-mediated oxazolidinone and the Crimmins' titanium-mediated oxazolidinethione aldol reactions are disclosed. A working hypothesis is put forth to explain the results.

Synthesis of Medium Ring Ethers. Part 4. Stereoselective Claisen-mediated Ring Expansion as a Route to Homochiral Disubstituted Medium Ring Lactones

Thermal elimination/Claisen rearrangement of selenoxides derived from the enantiomerically pure phenylselenomethyl-substituted cyclic acetals 4 and 8 proceeds stereospecifically to provide the homochiral 8- and 7-membered lactones 5 and 9 respectively.