445306-64-9

Upstream product

• 445306-63-8 4-[1-[2-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-allyl]-5-(tert-butyl-diphenyl-silanyloxy)-6-methoxymethoxy-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyloxy]-pentan-2-ol 
• 220351-82-6 (S)-3-((tert-butyldiphenylsilyl)oxy)dihydrofuran-2(3H)-one 
• 445306-74-1 (3S)-4-{(2R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-3-methylbutyronitrile 
• 445306-62-7 (4R)-5-{(2R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-4-methylpentan-2-one 
• 445306-72-9 (2R,6S)-2-{(2R)-6-[3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethanol 
• 445306-57-0 (2R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-2-[(2S)-(2-methyl-4-trimethylsilanylmethylpent-4-enyl)]-3,6-dihydro-2H-pyran 
• 445306-73-0 (2R,6S)-tert-butyl-(2-{6-[(2R)-3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethylsilane 
• 527743-03-9 toluene-4-sulfonic acid 3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl ester 
• 445306-75-2 1-{(2R)-2-methyl-3-[(2R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl]-propyl}vinyl trifluoromethanesulfonate 
• 445306-60-5 (3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enal 
• 445306-71-8 (3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol 
• 445306-61-6 (2E,7E,5S,6S)-5-(tert-butyldiphenylsilanyloxy)-6-(methoxymethoxy)-8-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-octa-2,7-dienoic acid N-methoxy-N-methyl-amide 
• 445306-58-1 (S)-diethyl [3-(tert-butyldiphenylsilanyloxy)-2-oxo-5-triethylsilanyloxy-pentyl]phosphonate 
• 445306-70-7 (1E,4S)-4-(tert-butyldiphenylsilanyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-6-(triethylsilanyloxy)-hex-1-en-3-one 

Downstream Products

• 445306-65-0 2-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-8-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-11-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-undeca-1,5,10-trien-4-ol 
• 115268-43-4 laulimalide 
• 445306-66-1 C₅₄H₈₄O₈Si₂ 

Relevant academic research and scientific papers

Total synthesis of the microtubule stabilizing antitumor agent laulimalide and some nonnatural analogues: The power of sharpless' asymmetric epoxidation

Three different routes are described for the synthesis of deoxylaulimalide (3), which is the immediate precursor of the marine sponge metabolite laulimalide (1). These routes mainly differ with respect to their ring closing step. Thus, route 1 uses a Still-Gennari olefination, route 2 a Yamaguchi lactonization, and route 3 an intramolecular allylsilane-aldehyde addition for establishing the macrocyclic structure. The unprotected deoxy derivative 3 was subjected to Sharpless' asymmetric epoxidation (SAE). With (R,R)-tartrate the 16,17-epoxide laulimalide (1) is formed selectively, whereas (S,S)-tartrate generates the 21,22-epoxide 142. This demonstrates the high reagent control involved in the SAE process, which in this case is used to achieve high stereo- and regioselectivity. Laulimalide and some derivatives thereof have been tested with respect to antitumor activity and compared to standard compounds paclitaxel and epothilone B.

Total synthesis of the antitumor agent (-)-laulimalide

A stereocontrolled synthesis of the title compound is described. Key steps are an allylsilane addition to a chiral acetal as the major coupling step and a Yamaguchi macrolactonization for ring closure.