545339-15-9

Upstream product

• 101711-78-8 (3R)-3-propionyl-4-benzyloxazolidin-2-one 
• 545339-14-8 (4R,5S,6S,Z)-5-[(tert-butyldimethylsilyl)oxy]-6-methoxy-2,4-dimethylocta-2,7-dienal 
• 56279-35-7 (E)-1-methoxy-2-methyl-1-penten-3-one 
• 72486-93-2 1-methoxy-2-methyl-3-trimethylsiloxy-1,3-pentadiene 
• 96-22-0 pentan-3-one 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 760988-93-0 (8R,9S,Z)-9-((S)-1-methoxyallyl)-2,2,3,3,6,8,11,11,12,12-decamethyl-4,10-dioxa-3,11-disilatridec-6-ene 
• 760988-61-2 (2S,3R)-2-((S)-1-Methoxy-allyl)-3,5-dimethyl-3,4-dihydro-2H-pyran-4-ol 
• 545339-13-7 (4R,5S,6S,Z)-5-[(tert-butyldimethylsilyl)oxy]-6-methoxy-2,4-dimethylocta-2,7-dien-1-ol 
• 545339-12-6 (4R,5S,6S,Z)-6-methoxy-2,4-dimethylocta-2,7-diene-1,5-diol 
• 545339-10-4 (2S,3S)-2-((S)-1-Methoxy-allyl)-3,5-dimethyl-2,3-dihydro-pyran-4-one 
• 545339-11-5 (5R,6S)-6-((S)-1-Methoxy-allyl)-3,5-dimethyl-5,6-dihydro-2H-pyran-2-ol 
• 545339-09-1 α-methoxy-α-vinyl aldehyde 
• 261631-96-3 (+)-(4S,5S)-4,5-bis[(1S)-1-methoxy-2-propenyl]-2,2-dimethyl-1,3-dioxolane 

Relevant academic research and scientific papers

The total synthesis of (+)-migrastatin

The first total synthesis of (+)-migrastatin, a macrolide natural product with interesting antimetastatic properties, has been accomplished. Our concise and flexible approach utilizes a Lewis acid-catalyzed diene aldehyde condensation to install the three

MIGRASTATIN ANALOGS IN THE TREATMENT OF CANCER

In one aspect, the present invention provides a method for treating colon and/or ovarian cancer in a subject comprising administering to a subject in need thereof a compound of general formula (I): wherein R1-R6, R, ,-R,, Q, Y1, Y2 and n are as defined herein, wherein the compound is present in an amount effective to inhibit colon and/or ovarian tumor metastasis.

The migrastatin family: Discovery of potent cell migration inhibitors by chemical synthesis

The first asymmetric total synthesis of (+)-migrastatin (1), a macrolide natural product with antimetastatic properties, has been accomplished. Our concise and flexible approach utilized a Lewis acid-catalyzed diene aldehyde condensation (LACDAC) to install the three contiguous stereocenters and the trisubstituted (Z)-alkene of migrastatin (2 + 3 → 21). Construction of the two remaining stereocenters and incorporation of the glutarimide-containing side chain was achieved by an anti-selective aldol addition of propionyl oxazolidinone 28 to angelic aldehyde 27, followed by a Horner-Wadsworth-Emmons (HWE) coupling of 32 with glutarimide aldehyde 5. Finally, the assembly of the macrocycle was realized by a highly (E)-selective ring-closing metathesis (35 → 37). Utilizing the power of diverted total synthesis (DTS), a series of otherwise inaccessible analogues was prepared and evaluated for their potential as tumor cell migration inhibitors in several in vitro assays. These studies revealed a dramatic increase in activity when the natural motif was considerably simplified, presenting macrolactones 45 and 48, as well as macrolactam 55, macroketone 60, and CF3-alcohol 71 as promising anti-metastatic agents.

MIGRASTATIN ANALOG COMPOSITIONS AND USES THEREOF

In one aspect, the present invention provides pharmaceutical compositions comprising a therapeutically effective amount of a compound of general formula (I), wherein R1-R6, Ra-RC, Q, Y1, Y2 and n are as defined herein, whereby the composition is formulated for administration to a subject at a dosage between about 0.1 mg/kg to about 50 mg/kg of body weight. In another aspect, the present invention provides a method for treating breast tumor metastasis in a subject comprising administering to a subject in need thereof a therapeutically effective amount of the inventive composition described directly above and a pharmaceutically acceptable carrier, adjuvant or vehicle.