1313274-96-2

Upstream product

• 863997-71-1 6-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-cyclohex-2-enone 
• 1313275-59-0 C₃₃H₄₂O₉Si 
• 1313275-61-4 C₃₁H₃₈O₈Si 
• 1313275-02-3 (S)-1-diazo-3-epoxy-5,5-dimethoxypenta-2,4-dione 
• 1313275-00-1 C₃₉H₅₄O₈Si₂ 
• 1313274-97-3 KCN-Triox₁ 
• 164264-14-6 (3S)-3-[(1,1-Dimethylethyl)dimethylsilyloxy]-oxolan-2-one 
• 4670-56-8 methyl 2-hydroxy-4-methylbenzoate 
• 50-85-1 2-hydroxy-p-toluic acid 
• 1313275-22-7 (2S,4S)-2-(tert-butyldimethylsilyloxy)-N-methoxy-4[(4-methoxybenzyl)oxy]-N-methylhex-5-enamide 
• 1335208-31-5 (2S,4S)-2-(tert-butyldimethylsilyloxy)-4-hydroxy-N-methoxy-N-methylhex-5-enamide 
• 1313275-21-6 (2S)-2-(tert-butyldimethylsilyloxy)-N-methoxy-N-methyl-4-oxobutanamide 
• 1313275-47-6 (2S)-2-(tert-butyldimethylsilyloxy)-4-hydroxy-N-methoxy-N-methylbutanamide 
• 1313275-14-7 2-(allyloxy)-N,N-diethyl-4-methylbenzamide 

Downstream Products

• 1335208-29-1 C₄₉H₆₂O₁₈Si 

Relevant academic research and scientific papers

TOTAL SYNTHESIS OF TRIOXACARCIN DC-45-A2 AND PREPARATION OF TRIOXACARCIN ANALOGS

In one aspect, the present invention provides novel derivatives of trioxacarin analogs of the formula (I) wherein the variables are as defined herein. The application also provides compositions, methods of treatment, and methods of synthesis thereof.

Total synthesis of trioxacarcin DC-45-A2

An enantioselective total synthesis of trioxacarcin DC-45-A2 (1) featuring a novel Lewis acid-induced cascade rearrangement of epoxyketone 6 to forge the polyoxygenated 2,7-dioxabicyclo[2.2.1]heptane core of the molecule is described.

Component-based syntheses of trioxacarcin A, DC-45-A1 and structural analogues

The trioxacarcins are polyoxygenated, structurally complex natural products that potently inhibit the growth of cultured human cancer cells. Here we describe syntheses of trioxacarcin A, DC-45-A1 and structural analogues by late-stage stereoselective glyc

A multiply convergent platform for the synthesis of trioxacarcins

Many first-line cancer drugs are natural products or are derived from them by chemical modification. The trioxacarcins are an emerging class of molecules of microbial origin with potent antiproliferative effects, which may derive from their ability to covalently modify duplex DNA. All trioxacarcins appear to be derivatives of a nonglycosylated natural product known as DC-45-A2. To explore the potential of the trioxacarcins for the development of smallmolecule drugs and probes, we have designed a synthetic strategy toward the trioxacarcin scaffold that enables access to both the natural trioxacarcins and nonnatural structural variants. Here, we report a synthetic route to DC-45-A2 froma differentially protected precursor, which in turn is assembled in just six steps from three components of similar structural complexity. The brevity of the sequence arises from strict adherence to a plan in which strategic bond-pair constructions are staged at or near the end of the synthetic route.

TRIOXACARCINS AND USES THEREOF

The present invention relates to trioxacarcin compounds of the formula: (I) or pharmaceutically acceptable forms thereof; wherein R1, R2, R3, R4, R5, R6, R7, R8, and R9 are as defined herein. The present invention also provides processes for preparing such compounds and intermediates thereto; pharmaceutical compositions comprising such compounds; and methods of use and treatment.