474432-75-2

Upstream product

• 123748-58-3 (3S)-3,7-dimethyl-oct-6-ene-1,3-diol 
• 98-59-9 p-toluenesulfonyl chloride 
• 82188-73-6 (2S,3S)-2,3-epoxygeraniol 
• 106-24-1 Geraniol 
• 166941-41-9 Toluene-4-sulfonic acid (2R,3S)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester 

Relevant academic research and scientific papers

First enantioselective total synthesis of the endogenous natriuretic agent LLU-α

The endogenous natriuretic agent LLU-α, 1, has been synthesized from geraniol 4 in 13 steps and 18% overall yield. The two key steps are a Gassman-Sato process to give the phenol 8 and cyclization of the triol 10 with acid to give the chroman 12 with retention of configuration at the tertiary alcohol center. Final oxidation gave 1.

Chemoselective reduction of 2,3-epoxy tosylates with DIBAL-H as a general route to enantiomerically-enriched 1-tosyloxy-2-alkanols

2,3-Epoxy tosylates may be reduced with DIBAL-H in CH2Cl2 or ether at -40°C to 1-tosyloxy-2-alkanols in high (94-98%) yields.