1404304-76-2

Upstream product

• 102517-37-3 (2R,3R)-1,2-epoxy-3-heptanol 
• 1404304-64-8 C₂₃H₃₂O₂Si 
• 33467-76-4 (E)-hept-2-en-1-ol 
• 1404304-70-6 C₂₆H₃₈O₂Si 
• 1404304-71-7 C₂₉H₄₀O₄Si 
• 68703-33-3 (E)-1-chloro-2-heptene 
• 1404304-67-1 C₂₇H₃₈O₃Si 
• 24850-33-7 allyltributylstanane 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 1404304-81-9 C₃₉H₆₆O₄Si₂ 
• 1404304-78-4 C₃₉H₆₄O₄Si₂ 
• 1404304-79-5 C₄₄H₇₄O₆Si₂ 
• 1404304-77-3 C₃₉H₆₄O₃Si₂ 

Relevant academic research and scientific papers

Enantioselective Synthesis of des-Epoxy-Amphidinolide N

The synthesis of des-epoxy-amphidinolide N was achieved in 22 longest linear and 33 total steps. Three generations of synthetic endeavors are reported herein. During the first generation, our key stitching strategy that highlighted an intramolecular Ru-catalyzed alkene-alkyne (Ru AA) coupling and a late-stage epoxidation proved successful, but the installation of the α,α′-dihydroxyl ketone motif employing a dihydroxylation method was problematic. Our second generation of synthetic efforts addressed the scalability problem of the southern fragment synthesis and significantly improved the efficiency of the atom-economical Ru AA coupling, but suffered from several protecting group-based issues that proved insurmountable. Finally, relying on a judicious protecting group strategy together with concise fragment preparation, des-epoxy-amphidinolide N was achieved in a convergent fashion. Calculations disclose a hydrogen-bonding bridge within amphidinolide N. Comparisons of 13C NMR chemical shift differences using our synthetic des-epoxy-amphidinolide N suggest that amphidinolide N and carbenolide I are probably identical.

Diastereoselective formation of tetrahydrofurans via pd-catalyzed asymmetric allylic alkylation: Synthesis of the C13-C29 subunit of amphidinolide N

An efficient synthesis of the C13-C29 fragment of amphidinolide N is described. The synthesis relies on a new strategy involving Pd-catalyzed asymmetric allylic alkylation to generate diastereoselectively the cis- or trans-THF unit simply by varying the enantiomer of the ligand. The C19 hydroxyl-bearing stereocenter was introduced using a chelation-controlled allylation which led exclusively to a single diastereoisomer.