128693-46-9

Upstream product

• 63930-49-4 (R)-3-(benzyloxy)-2-methylpropan-1-ol 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 104265-24-9 (3R)-4-benzyloxy-3-methyl-butanonitrile 
• 394657-32-0 [(2R,4S)-4-(1-Ethoxy-allyloxy)-2-methyl-hept-6-enyloxymethyl]-benzene 
• 90865-70-6 [3R]-4-Benzyloxy-3-methylbutanal 
• 273733-89-4 (4S,6R)-7-(benzyloxy)-6-methylhept-1-en-4-ol 
• 273733-91-8 (S)-6-((R)-3-(benzyloxy)-2-methylpropyl)-5,6-dihydro-2H-pyran-2-one 
• 1027233-25-5 Acetic acid (S)-6-((R)-3-benzyloxy-2-methyl-propyl)-5,6-dihydro-2H-pyran-2-yl ester 
• 273733-92-9 (2S,6R)-6-allyl-2-[(2R)-3-benzyloxy-2-methyl-propyl]-3,6-dihydro-2H-pyran 
• 273733-90-7 (2R,4S)-1-benzyloxy-2-methyl-6-hepten-4-yl-propenoate 
• 312695-89-9 2-[(2R,6S)-6-((R)-3-Benzyloxy-2-methyl-propyl)-5,6-dihydro-2H-pyran-2-yl]-ethanol 
• 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 

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.

An enantioselective synthesis of the C2-C16 segment of antitumor macrolide laulimalide

An enantioselective synthesis of the C2-C16 segment of the novel antitumor agent laulimalide is described. The key steps involve a highly diastereoselective allylation, ring-closing olefin metathesis of a homoallylic alcohol derived acrylate ester, a stereoselective anomeric alkylation and an elaboration of an exo-methylene unit by a Julia olefination reaction. (C) 2000 Elsevier Science Ltd.