158783-80-3

Upstream product

• 944913-77-3 C₃₈H₆₆O₆Si₂ 
• 158783-79-0 Acetic acid (1R,2S,3S,4S)-1-[(R)-1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-ethyl]-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-pentyl ester 
• 158783-78-9 2-Ethyl-6-((1R,2S,3R,5S)-2-hydroxy-1,3,5-trimethyl-4-oxo-6-triisopropylsilanyloxy-hexyl)-3,5-dimethyl-pyran-4-one 
• 158783-76-7 (S)-2-methyl-1-(triisopropylsilyloxy)pentan-3-one 

Downstream Products

• 123003-47-4 (+)-baconipyrone C 
• 944913-78-4 (2R,3R,4S,6S)-6-(6-Ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-5-oxo-heptanoic acid 
• 944913-82-0 C₃₇H₅₂O₉ 
• 1026344-34-2 (2R,3S,4S,6S)-6-(6-Ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-5-oxo-heptanal 

Relevant academic research and scientific papers

Chiral N-heterocyclic carbenes in natural product synthesis: Application of Ru-catalyzed asymmetric ring-opening/cross-metathesis and Cu-catalyzed allylic alkylation to total synthesis of baconipyrone C

(Chemical Equation Presented) Chiral carbenes as major players: Two recently discovered chiral N-heterocyclic carbene (NHC) complexes play a crucial role in a concise enantioselective total synthesis of baconipyrone C (see scheme). An (NHC)Cu complex catalyzes a double asymmetric allylic alkylation (AAA), and an (NHC)Ru complex catalyzes an asymmetric ring-opening/cross- metathesis (AROM/CM) to establish the absolute configuration of the target. RCM = ring-closing metathesis.

Assignment of the Absolute Configuration of the Siphonarins and Baconipyrones. Enantiocontrolled Synthesis of a γ-Pyrone Subunit.

Aldehyde 11 was prepared with >90percent ds using a Sn(II)-mediated aldol reaction between (S)-13 and (S)-14.Conversion into the γ-pyrone 8, a known degradation product from dihydrosiphonarin B, established the absolute configuration as enantiomeric to th