193416-33-0

Upstream product

• 142860-84-2 4-(p-methoxybenzyloxy)-1,2-epoxybutane 
• 142860-83-1 1-(4-methoxybenzyloxy)-3-butene 
• 824-94-2 p-methoxybenzyl chloride 
• 128461-65-4 3-(p-methoxybenzyloxy)propanal 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 193416-54-5 (E)-6-(4-methoxybenzyloxy)-1,3-hexen-2-one 

Downstream Products

• 529494-85-7 (2S,6S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-6-(2-((4-methoxybenzyl)oxy)ethyl)dihydro-2H-pyran-4(3H)-one 
• 193416-35-2 C₂₆H₄₂O₆Si 
• 1262749-70-1 C₄₃H₆₅NO₅Si₂ 
• 1262749-72-3 C₃₁H₅₁NO₇Si 
• 193416-47-6 (2S,6R)-1-[(2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-yl]-8-(4-methoxy-benzyloxy)-4-methylene-6-triethylsilanyloxy-octan-2-ol 
• 193416-49-8 (2R,6R)-1-[(2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-yl]-8-(4-methoxy-benzyloxy)-4-methylene-6-triethylsilanyloxy-octan-2-ol 
• 193416-51-2 Methanesulfonic acid (1S,5R)-1-[(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-ylmethyl]-7-(4-methoxy-benzyloxy)-3-methylene-5-triethylsilanyloxy-heptyl ester 
• 193416-64-7 Methanesulfonic acid (1S,5R)-1-[(2S,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-ylmethyl]-5-hydroxy-7-(4-methoxy-benzyloxy)-3-methylene-heptyl ester 
• 193416-31-8 (R)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethylamine 
• 193416-53-4 (S)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethanol 
• 193416-52-3 tert-Butyl-((2R,4R,6R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-4-yloxy)-diphenyl-silane 
• 193416-65-8 (S)-1-((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(2R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-tetrahydro-pyran-2-yl)-ethane-1,2-diol 
• 193416-56-7 tert-Butyl-{(2R,4R,6R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-4-yloxy}-diphenyl-silane 
• 193416-41-0 [(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-yl]-acetaldehyde 

Relevant academic research and scientific papers

Stereocontrolled total synthesis of (+)-leucascandrolide A

Apparently no longer available from its natural source is the potent cytotoxic and antifungal agent leucascandrolide A (1), which was initially isolated from a New Caledonian calcareous sponge. A highly stereocontrolled total synthesis of this structurally unique macrolide commences with a Jacobsen asymmetric hetero Diels-Alder reaction to configure the tetrahydropyran ring. An efficient endgame relies on two Mitsunobu reactions, the first to generate the 18-membered macrolactone and the second to attach the oxazole-bearing side chain.

A fully stereocontrolled total synthesis of (+)-leucascandrolide A

A highly stereocontrolled total synthesis of leucascandrolide A, a cytotoxic 18-membered macrolide from the calcareous sponge Leucascandra caveolata, starts out with a Jacobsen asymmetric hetero Diels-Alder reaction to configure the 2,6-cis-tetrahydropyran ring. All the remaining oxygenated stereocentres are introduced with high selectivity by relying on substrate-based control. An efficient endgame depends on two Mitsunobu reactions, the first to close the macrolactone with inversion at C17 and the second to attach the oxazole-containing side chain at C5, followed by Lindlar hydrogenation of the two alkynes to provide (+)-leucascandrolide A.