848187-93-9

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 848188-03-4 (E)-(R)-4-{(2R,3R,4R,5S)-3,4-Dihydroxy-5-[2-(1-phenyl-1H-tetrazole-5-sulfonyl)-ethyl]-tetrahydro-pyran-2-yl}-3-methyl-4-triisopropylsilanyloxy-but-2-enoic acid ethyl ester 
• 848187-92-8 (E)-(R)-3-Methyl-4-{(2R,5R)-5-[2-(1-phenyl-1H-tetrazole-5-sulfonyl)-ethyl]-5,6-dihydro-2H-pyran-2-yl}-4-triisopropylsilanyloxy-but-2-enoic acid ethyl ester 
• 848188-01-2 (E)-(R)-4-[(2R,5R,6S)-6-Ethoxy-5-(3-methyl-but-2-enyl)-5,6-dihydro-2H-pyran-2-yl]-3-methyl-4-triisopropylsilanyloxy-but-2-enoic acid ethyl ester 
• 848187-91-7 (E)-(R)-4-[(2R,5R,6S)-6-Ethoxy-5-(2-hydroxy-ethyl)-5,6-dihydro-2H-pyran-2-yl]-3-methyl-4-triisopropylsilanyloxy-but-2-enoic acid ethyl ester 
• 848188-02-3 (E)-(R)-4-[(2R,5R)-5-(2-Hydroxy-ethyl)-5,6-dihydro-2H-pyran-2-yl]-3-methyl-4-triisopropylsilanyloxy-but-2-enoic acid ethyl ester 
• 848188-00-1 (E)-(R)-4-[(2R,5R,6S)-6-Ethoxy-5-(3-methyl-but-2-enyl)-5,6-dihydro-2H-pyran-2-yl]-4-hydroxy-3-methyl-but-2-enoic acid ethyl ester 
• 62054-49-3 ethyl (E)-3-formyl-2-butenoate 

Relevant academic research and scientific papers

Catalytic asymmetric synthesis of a potent thiomarinol antibiotic

Thiomarinols, isolated from the bacterium Alteromonas rava sp. nov. SANK 73390, are potent marine antibiotics that possess both Gram-positive and Gram-negative activity. The first total synthesis of a member of the thiomarinol class of marine antibiotics was achieved in a remarkable global yield of 22% (from 3-boronoacrolein pinacolate). The highlight of this synthesis is the efficient catalytic enantio-, regio-, E/Z-, and diastereoselective three-component inverse electron demand Diels-Alder/allylboration sequence. This key operation provides a rare example of an enantioselective HDA reaction involving acyclic 2-substituted enol ethers, and it featured an unusual but fortuitous kinetic selection that favored the requisite Z-dienophile. Copyright