529494-91-5

Upstream product

• 618096-60-9 (4S,5R,7R)-8-{(2R,4R,6S)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-4-methyl-octane-1,5,7-triol 
• 529494-89-1 (4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-1-{(2S,4R,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octan-2-one 
• 529494-90-4 (2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4R,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol 
• 618096-85-8 (2S,4R,6S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran 
• 529494-88-0 Triisopropyl-{(2S,4S,6R)-2-[2-(4-methoxy-benzyloxy)-ethyl]-6-prop-2-ynyl-tetrahydro-pyran-4-yloxy}-silane 
• 529494-82-4 1-{(2S,4R,6S)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propan-2-one 
• 529494-87-9 (2S,4R,6R)-tetrahydro-2-hydroxymethyl-4-(triisopropylsilyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-2H-pyran 
• 529494-86-8 (2S,4R,6S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-4-ol 
• 529494-85-7 (2S,6S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-6-(2-((4-methoxybenzyl)oxy)ethyl)dihydro-2H-pyran-4(3H)-one 
• 193416-54-5 (E)-6-(4-methoxybenzyloxy)-1,3-hexen-2-one 
• 193416-33-0 Triethyl-[(E)-5-(4-methoxy-benzyloxy)-1-methylene-pent-2-enyloxy]-silane 

Downstream Products

• 529494-92-6 (5S,6R)-6-((S)-2-Methoxy-3-{(2R,4R,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-one 
• 529494-93-7 (E)-1-[(2S,5S,6R)-6-((S)-2-Methoxy-3-{(2R,4R,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-one 
• 529494-94-8 (E)-(S)-1-[(2S,5S,6R)-6-((S)-2-Methoxy-3-{(2R,4R,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol 
• 618096-83-6 Acetic acid (E)-(S)-1-[(2S,5S,6R)-6-((S)-2-methoxy-3-{(2R,4R,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-5-methyl-hex-2-enyl ester 

Relevant academic research and scientific papers

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.

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.