1554478-10-2

Upstream product

• 1554478-16-8 C₃₀H₄₀O₆ 
• 1554478-13-5 C₄₁H₆₁NO₁₁Si 
• 1140836-32-3 methyl α-benzyloxyphenyllactate 
• 1554478-22-6 C₃₄H₅₅NO₁₁Si 
• 1554478-28-2 C₄₄H₆₅NO₁₃Si 
• 1554478-34-0 C₃₀H₄₂O₆ 
• 1554478-37-3 C₃₀H₄₂O₆ 
• 2592-18-9 Boc-Thr-OH 
• 898543-62-9 2S-hydroxy-3S-methylpentanoic acid allyl ester 
• 488-15-3 (2S,3S)-2-Hydroxy-3-methylpentanoic acid 
• 295360-72-4 5-(phenethylthio)-1-phenyl-1H-tetrazole 
• 73-32-5 L-isoleucine 

Downstream Products

• 1554478-08-8 C₃₁H₄₃NO₁₁ 
• 1554478-31-7 C₄₁H₄₆N₂O₁₂ 

Relevant academic research and scientific papers

Total Synthesis of the GRP78-Downregulatory Macrolide (+)-Prunustatin A, the Immunosuppressant (+)-SW-163A, and a JBIR-04 Diastereoisomer That Confirms JBIR-04 Has Nonidentical Stereochemistry to (+)-Prunustatin A

A unified total synthesis of the GRP78-downregulator (+)-prunustatin A and the immunosuppressant (+)-SW-163A based upon [1 + 1 + 1 + 1]-fragment condensation and macrolactonization between O(4) and C(5) is herein described. Sharpless asymmetric dihydroxylation was used to set the C(2) stereocenter present in both targets. In like fashion, coupling of the (+)-prunustatin A macrolide amine with benzoic acid furnished a JBIR-04 diastereoisomer whose NMR spectra did not match those of JBIR-04, thus confirming that it has different stereochemistry than (+)-prunustatin A.

First total synthesis of prunustatin A

In this study, we achieved the first total synthesis of natural prunustatin A (1), a novel inhibitor of glucose-regulated protein 78 (GRP78) expression. A key feature included a 15-membered ring macrocyclization, which was successfully accomplished by employing Shiina macrolactonization using 2-methyl-6- nitrobenzoic anhydride (MNBA) and 4-dimethylaminopyridine (DMAP).