146478-72-0

Usage

Uses

Since the provided materials do not specify the uses of 4(S)-Acetoxy-N-[(2R,3R,5S,6S)-6-[5-[(3R,4R,5R,7S)-4,7-dihydroxy-7-methyl-1,6-dioxaspiro[2.5]octan-5-yl]-3-methyl-2(E),4(E)-pentadienyl]-2,5-dimethyltetrahydropyran-3-yl]-2(Z)-pentenamide, it is not possible to list its applications based on the given information. However, given the molecule's complex structure and the presence of various functional groups, it may have potential uses in pharmaceuticals, materials science, or as a synthetic intermediate in organic chemistry. Further research and experimentation would be required to determine its specific applications and benefits in these or other fields.

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 
• 310398-03-9 Acetic acid (Z)-(S)-3-{(2R,3R,5S,6S)-6-[(2E,4E)-5-((3R,4R,5R,7R)-7-iodomethyl-4-triethylsilanyloxy-1,6-dioxa-spiro[2.5]oct-5-yl)-3-methyl-penta-2,4-dienyl]-2,5-dimethyl-tetrahydro-pyran-3-ylcarbamoyl}-1-methyl-allyl ester 
• 310398-02-8 {(3R,4R,5R,7R)-5-[(1E,3E)-5-((2S,3S,5R,6R)-5-Azido-3,6-dimethyl-tetrahydro-pyran-2-yl)-3-methyl-penta-1,3-dienyl]-7-iodomethyl-1,6-dioxa-spiro[2.5]oct-4-yloxy}-triethyl-silane 

Downstream Products

• 391611-36-2 spliceostatin A 

Relevant academic research and scientific papers

Enantioselective syntheses of FR901464 and spliceostatin A: Potent inhibitors of spliceosome

Enantioselective syntheses of FR901464 and spliceostatin A, potent spliceosome inhibitors, are described. The synthesis of FR901464 has been accomplished in a convergent manner in 10 linear steps (20 total steps). The A-tetrahydropyran ring was constructed from (R)-isopropylidene glyceraldehyde. The functionalized tetrahydropyran B-ring was synthesized utilizing a Corey-Bakshi-Shibata reduction, an Achmatowicz reaction, and a stereoselective Michael addition as the key steps. Coupling of A- and B-ring fragments was accomplished via cross-metathesis.

Enantioselective total syntheses of fr901464 and spliceostatin a and evaluation of splicing activity of key derivatives

FR901464 (1) and spliceostatin A (2) are potent inhibitors of spliceosomes. These compounds have shown remarkable anticancer activity against multiple human cancer cell lines. Herein, we describe efficient, enantioselective syntheses of FR901464, spliceostatin A, six corresponding diastereomers and an evaluation of their splicing activity. Syntheses of spliceostatin A and FR901464 were carried out in the longest linear sequence of 9 and 10 steps, respectively. To construct the highly functionalized tetrahydropyran A-ring, we utilized CBS reduction, Achmatowicz rearrangement, Michael addition, and reductive amination as key steps. The remarkable diastereoselectivity of the Michael addition was specifically demonstrated with different substrates under various reaction conditions. The side chain B was prepared from an optically active alcohol, followed by acetylation and hydrogenation over Lindlars catalyst. The other densely functionalized tetrahydropyran C-ring was derived from readily available (R)-isopropylidene glyceraldehyde through a route featuring 1,2-addition, cyclic ketalization, and regioselective epoxidation. These fragments were coupled together at a late stage through amidation and cross-metathesis in a convergent manner. Six key diastereomers were then synthesized to probe the importance of specific stereochemical features of FR901464 and spliceostatin A, with respect to their in vitro splicing activity.

FR901464 AND ANALOGS WITH ANTITUMOR ACTIVITY AND METHOD FOR THEIR PREPARATION

The present invention provides analogs of FR901464, as well as a 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 associated with dysfunctional RNA splicing.

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 synthesis of FR901464: Second generation

FR901464, a potent cell cycle inhibitor, was synthesized in a convergent manner using natural chiral pool, l-threonine, ethyl (S)-lactate and 2-deoxy-d-glucose as starting materials.

Total synthesis of FR901464, an antitumor agent that regulates the transcription of oncogenes and tumor suppressor genes

FR901464 is a potent anticancer agent that regulates the transcription of oncogenes and tumor suppressor genes. A convergent enantioselective synthesis of FR901464 was accomplished in 13 linear steps. Central to the synthetic approach was the diene-ene cr

FR901464: Total synthesis, proof of structure, and evaluation of synthetic analogues

The natural product FR901464 (1) was isolated by the Fujisawa Pharmaceutical Co. and shown to have intriguing biological properties including impressive antitumor activity. In this paper we describe the first total synthesis of 1 in full detail. A chiral building block synthetic strategy was used to assemble the target: optically active components were generated using asymmetric catalytic reactions, and these fragments were coupled together at a late stage in a convergent synthesis. In particular, a versatile, asymmetric hetero-Diels-Alder (HDA) reaction was developed in the context of this synthesis and used with great effectiveness for the preparation of the two densely functionalized pyran rings. The flexible nature of the synthetic route also allowed us to prepare a series of analogues of 1. These compounds were used to prove the relative stereochemistry of the natural product as well as to probe the importance of certain structural features of FR901464 with regard to biological activity.

A synthesis of FR901464

FR901464, a potent cell cycle inhibitor, was synthesized in a convergent manner using natural chiral pool, L-threonine, ethyl (S)-lactate and 2-deoxy-D-glucose as starting materials.