933474-26-1

Upstream product

• 882028-31-1 (S,Z)-5-(((2R,3R,5S,6S)-2,5-dimethyl-6-((E)-3-methylpenta-2,4-dien-1-yl)tetrahydro-2H-pyran-3-yl)amino)-5-oxopent-3-en-2-yl acetate 
• 933190-01-3 (3R,4R,5R)-7,7-dimethyl-5-vinyl-1,6-dioxaspiro[2.5]octan-4-ol 
• 263881-01-2 (4R,5R)-4-t-butoxycarbonylamino-2-methylhexan-5-olide 
• 882028-41-3 tert-butyl ((2R,3R)-2,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-3-yl)carbamate 
• 263881-23-8 (S,Z)-4-((tert-butyldiphenylsilyl)oxy)pent-2-enoic acid 
• 189631-15-0 methyl (S,Z)-4-((tert-butyldiphenylsilyl)oxy)pent-2-enoate 
• 882028-43-5 tert-butyl [(2R,3R,5S,6S)-2,5-dimethyl-6-(prop-2-en-1-yl)tetrahydro-2H-pyran-3-yl]carbamate 
• 882028-42-4 tert-butyl ((2R,3R,5S)-6-allyl-6-hydroxy-2,5-dimethyltetrahydro-2H-pyran-3-yl)carbamate 
• 878673-43-9 tert-butyl ((2R,3R,5S)-2,5-dimethyl-6-oxotetrahydro-2H-pyran-3-yl)carbamate 
• 310397-89-8 (Z)-(4S)-4-acetoxypent-2-enoic acid 
• 310397-95-6 (S)-4-acetoxypent-2-ynoic acid 
• 52804-46-3 5-[(tetrahydro-2H-pyran-2-yl)oxy]pent-3-yn-2-one 

Relevant academic research and scientific papers

MEAYAMYCIN ANALOGUES AND METHODS OF USE

Compounds according to formula (I), where R is as defined herein, have anti-cancer properties.

Total Synthesis of Meayamycin and O-Acyl Analogues

A short, scalable total synthesis of meayamycin is described by an approach that entails a longest linear sequence of 12 steps (22 steps overall) from commercially available chiral pool materials (ethyl l-lactate, BocNH-Thr-OH, and d-ribose) and introduces the most straightforward preparation of the right-hand subunit detailed to date. The use of the approach in the divergent synthesis of a representative series of O-acyl analogues is exemplified.

SYNTHESIS OF FR901464 AND ANALOGS WITH ANTITUMOR ACTIVITY

The present invention provides novel analogs of FR901464, as well as an improved methodology for preparing FR901464 and its analogs. These compounds display an anti-cancer activity and are candidates for therapies against a number of disease states associ

Total syntheses, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue

FR901464 is a potent anticancer natural product that lowers the mRNA levels of oncogenes and tumor suppressor genes. In this article, we report a convergent enantioselective synthesis of FR901464, which was accomplished in 13 linear steps. Central to the synthetic approach was the diene-ene cross olefin metathesis reaction to generate the C6-C7 olefin without the use of protecting groups as the final step. Additional key reactions include a Zr/Ag-promoted alkynylation to set the C4 Stereocenter, a mild and chemoselective Red-Al reduction, a reagent-controlled stereoselective Mislow-Evans-type [2,3]-sigmatropic rearrangement to install the C5 Stereocenter, a Carreira asymmetric alkynylation to generate the C4′ stereocenter, and a highly efficient ring-closing metathesis-allylic oxidation sequence to form an unsaturated lactone. The decomposition pathways of FR901464's right fragment were studied under physiologically relevant conditions. Facile epoxide opening by β-elimination gave two enones, one of which could undergo dehydration via its hemiketal to form a furan. To prevent this decomposition pathway, a right fragment was rationally designed and synthesized. This analogue was 12 times more stable than the right fragment of the natural product. Using this more stable right fragment analogue, an FR901464 analogue, meayamycin, was prepared in 13 linear steps. The inhibitions of human breast cancer MCF-7 cell proliferation by synthetic FR901464 and meayamycin were studied, and the GI50 values for these compounds were determined to be 1.1 nM and 10 pM, respectively. Thus, meayamycin is among the most potent anticancer small molecules that do not bind to either DNA or microtubule.