349539-60-2

Upstream product

• 90865-70-6 [3R]-4-Benzyloxy-3-methylbutanal 
• 289473-02-5 (1E,3S,4S)-6-benzenesulfonyl-4-(4-methoxy-benzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-1-en-3-ol 
• 312695-75-3 [(2R,6R),(2S),2S]-4-(3-{6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methylpropyl)-2-methoxymethoxypent-4-enal 
• 312695-80-0 (S)-2-Benzenesulfonyl-2-((R)-3-{(2R,6R)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-5-(4-methoxy-benzyloxy)-pentane-1,4-diol 
• 312695-79-7 (S)-3-Benzenesulfonyl-3-((R)-3-{(2R,6R)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-5-(4-methoxy-benzyloxymethyl)-dihydro-furan-2-one 
• 385809-16-5 (2R,6R)-tert-butyl-[2-(6-{4-[(2S)-3-(4-methoxybenzyloxy)-2-methoxymethoxy-propyl]-[(2S)-2-methylpent-4-enyl]}-5,6-dihydro-2H-pyran-2-yl)-ethoxy]-dimethylsilane 
• 312695-81-1 4-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-1-(4-methoxy-benzyloxy)-pent-4-en-2-ol 
• 312695-91-3 (2S)-4-(3-{(2R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-(2S)-2-methylpropyl)-2-methoxymethoxy-pent-4-en-1-ol 
• 312695-77-5 (2R,6S)-(2-{6-[(2R)-3-benzyloxy-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-tert-butyl-dimethyl-silane 
• 312695-78-6 (2R,6S)-tert-butyl-(2-{6-[(2R)-3-iodo-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethyl-silane 
• 312695-90-2 (2R)-3-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methylpropan-1-ol 
• 312695-89-9 2-[(2R,6S)-6-((R)-3-Benzyloxy-2-methyl-propyl)-5,6-dihydro-2H-pyran-2-yl]-ethanol 
• 289473-04-7 (3S,4S)-6-Benzenesulfonyl-4-(4-methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-1-yn-3-ol 
• 289473-01-4 (4S)-6-benzenesulfonyl-4-(4-methoxy-benzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-1-yn-3-one 

Downstream Products

• 349539-62-4 2-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-(4-Methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-ethanol 
• 394657-50-2 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethyl ester 
• 349539-64-6 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethoxymethyl ester 

Relevant academic research and scientific papers

Total synthesis of microtubule-stabilizing agent (-)-laulimalide

An enantioselective first total synthesis of laulimalide (1) is described. Laulimalide, a remarkably potent antitumor macrolide, has been isolated from the Indonesian sponge Hyattella sp. and the Okinawan sponge Fasciospongia rimosa. Laulimalide represents a new class of antitumor agents with significant clinical potential. The synthesis is convergent and involved the assembly of C3-C16 segment 4 and C17-C28 segment 5 by Julia olefination. The sensitive C2-C3 cis-olefin functionality was installed by Yamaguchi macrolactonization of a hydroxy alkynic acid followed by hydrogenation of the resulting alkynoic lactone over Lindlar's catalyst. Initial attempts of intramolecular Still's variant of Horner - Emmons olefination between the C19-phosphonocetate and C3-aldehyde provided a 1:2 mixture of cis- and trans-macrolactones. The trans-isomer was photo-isomerized to a mixture of cis- and trans-isomers. The other key steps involved ring-closing olefin metathesis to construct both dihydropyran units, stereoselective anomeric alkylation to functionalize the dihydropyran ring, stereoselective reduction of the resulting alkynyl ketone to set the C20-hydroxyl stereochemistry, and a novel Julia olefination protocol for the installation of the C13-exomethylene unit. The sensitive epoxide at C16-C17 was introduced in a highly stereoselective manner by Sharpless epoxidation at the final stage of the synthesis.