103563-54-8

Upstream product

• 103563-47-9 (Z)-6-Benzyloxymethoxy-3-ethyl-4-trimethylsilanyl-hex-4-ene-2,3-diol 
• 111149-29-2 (R)-(Z)-1-benzyloxy-2-(3'-trimethylsilylpropargyloxy)-3-pentene 
• 120448-40-0 (R)-(Z)-1-benzyloxy-2-propargyloxy-3-pentene 
• 141858-86-8 (4S,5R)-(E)-1-benzyloxy-5-tert-butyldimethylsilyloxy-4-methyl-2-heptene 
• 111149-40-7 (3R,4S)-(E)-7-benzyloxy-4-methylhept-5-en-3-ol 
• 110339-29-2 (R)-(Z)-1-Benzyloxy-2-hydroxy-3-pentene 
• 141858-87-9 (4S,5R,E)-5-[(tert-butyldimethylsilyl)oxy]-4-methylhept-2-en-1-ol 
• 120448-41-1 (3R,4S)-(E)-7-benzyloxy-4-methylhept-5-en-1-yn-3-ol 
• 123372-87-2 (3S,4S)-(E)-7-benzyloxy-4-methylhept-5-en-1-yn-3-ol 
• 141207-20-7 Benzoic acid (E)-(1S,2S)-5-benzyloxy-1-ethynyl-2-methyl-pent-3-enyl ester 
• 111149-31-6 (3R,4S)-(E)-7-benzyloxy-4-methyl-1-trimethylsilylhept-5-en-1-yn-3-ol 
• 103563-33-3 (S)-(Z)-6-<(benzyloxy)methoxy>-2-hydroxy-4-(trimethylsilyl)-4-hexen-3-one 
• 103563-34-4 Methanesulfonic acid (Z)-(S)-5-benzyloxymethoxy-1-methyl-2-oxo-3-trimethylsilanyl-pent-3-enyl ester 
• 103563-51-5 (R)-(Z)-7-<(benzyloxy)methoxy>-4-methyl-5-(trimethylsilyl)-5-hepten-3-one 

Downstream Products

• 103563-76-4 Phenoxy-acetic acid (E)-(1R,2S)-1-ethyl-2-methyl-5-oxo-pent-3-enyl ester 
• 103563-75-3 Phenoxy-acetic acid (E)-(1R,2S)-1-ethyl-5-hydroxy-2-methyl-pent-3-enyl ester 
• 79495-87-7 protomycinolide IV 

Relevant academic research and scientific papers

AN ENANTIOCONTROLLED ROUTE TO PROTOMYCINOLIDE IV AND ITS PRESUMED BIOGENETIC PRECURSORS USING (S)-O-BENZYLGLYCIDOL

Starting with (S)-O-benzylglycidol (9) as only chiral building block, a formal synthesis of protomycinolide IV (1) and the first syntheses of its presumed biogenetic precursors methyl epimycinonate I (2), methyl mycinonate I (3), methyl mycinonate II (4),

STEREOSELECTIVE SYNTHESIS OF C(1)-C(9) AND C(11)-C(17) FRAGMENTS OF PROTOMYCINOLIDE IV BASED ON ASYMMETRIC PINACOL-TYPE REARRANGEMENT

Two chiral intermediates, C(1)-C(9) and C(11)-C(17) portions of protomycinolide IV, were synthesized both from (S)-ethyl lactate via asymmetric pinacol-type rearrangement followed by diastereoselective reactions on α-methyl-β,γ-unsaturated carbonyl compounds.