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Usage

Uses

Used in Anticancer Applications:
Pederin is used as an anticancer agent for its ability to inhibit protein biosynthesis and mitosis, effectively targeting and disrupting the growth of cancer cells.
Used in Pharmaceutical Research:
Pederin is utilized in pharmaceutical research as a promising candidate for the development of new cancer treatments due to its potent antitumor properties and unique mechanism of action.
Used in Drug Delivery Systems:
Similar to gallotannin, pederin can also be incorporated into drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes in cancer treatment. Various organic and metallic nanoparticles can be employed as carriers for pederin delivery, aiming to improve its overall effectiveness against cancer cells.

Enzyme inhibitor

pederine and paederine, from the blister beetle Paederus fuscipes inhibits eukaryotic protein biosynthesis and mitosis, even at concentrations of 2–3 nM. 1. Carrasco, Battaner & Vazquez Meth. Enzymol. 30, 282. 2. Jiménez Trends Biochem. Sci

InChI:InChI=1/C25H45NO9/c1-14-12-25(33-9,35-16(3)15(14)2)21(28)22(29)26-23(32-8)18-11-19(27)24(4,5)20(34-18)10-17(31-7)13-30-6/h15-21,23,27-28H,1,10-13H2,2-9H3,(H,26,29)

Upstream product

• 85279-96-5 methyl benzoylpedimidate 
• 73787-23-2 (+)-benzoylpedamide 
• 1750-73-8 2,2-dimethyl-3-oxo-butanal 
• 956117-45-6 (S)-2-chloro-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-oxoethyl benzoate 
• 175085-05-9 (S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid 
• 1271737-46-2 C₃₈H₆₃NO₁₀Si 
• 1271737-45-1 (2S,4R,6R)-6-((S)-2,3-dimethoxypropyl)-5,5-dimethyl-4-((triethylsilyl)oxy)tetrahydro-2H-pyran-2-carbonitrile 
• 1271737-42-8 (2S,4R,6R)-1-methoxy-5,5-dimethyl-6-((triethylsilyl)oxy)non-8-ene-2,4-diol 
• 1271737-44-0 (2S,4R,6R)-6-((S)-2-hydroxy-3-methoxypropyl)-5,5-dimethyl-4-((triethylsilyl)oxy)tetrahydro-2H-pyran-2-carbonitrile 
• 869964-37-4 (4S)-4-triethylsilanyloxy-3,3-dimethylhept-6-en-2-one 
• 869964-24-9 (4S)-4-hydroxy-3,3-dimethylhept-6-en-2-one 
• 956117-56-9 C₄₁H₆₉NO₁₂Si₂ 
• 87045-87-2 (R)-((2R,4R,5R,6R)-4-Bromomethyl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-hydroxy-acetic acid methyl ester 
• 87045-86-1 methyl (αS,2R,4R,5R,6R)-4-(bromomethyl)tetrahydro-α-hydroxy-2-methoxy-5,6-dimethyl-2H-pyran-2-acetate 

Downstream Products

• 123483-10-3 (+)-dibenzoylpederin 

Relevant academic research and scientific papers

A synthesis of (+)-pederin. The metallated dihydropyran approach

The addition of a 6-lithio-3,4-dihydro-2H-pyran to a methyl oxamate ester in the presence of TMEDA is a key step in the synthesis of a masked 1,2,3-tricarbonyl moiety used to construct the N-(1-alkoxy-1-alkyl)-amide bridge of the potent cytotoxic agent pederin. A Pd(0)-catalysed stannylation of an O-trifluoromethylsulfonyl ketene acetal provides an efficient synthesis of the 6-(trimethylstannyl)-3,4-dihydro-2H-pyran which transmetallates to the lithium derivative on treatment with n-BuLi.

PEDERIN AND PSYMBERIN AGENTS

Compounds that include a pederin, psymberin or pederin/psymberin chimera scaffold. The pederin scaffold includes a substituent at the C10 and/or C13 position that may include a linker that may be conjugated to a targeting moiety. The psymberin scaffold in

Total synthesis and biological evaluation of pederin, psymberin, and highly potent analogs

The potent cytotoxins pederin and psymberin have been prepared through concise synthetic routes (10 and 14 steps in the longest linear sequences, respectively) that proceed via a late-stage multicomponent approach to construct the N-acyl aminal linkages.

Total synthesis of pederin and analogues

A ten-step program: The potent cytotoxin pederin and several analogues have been prepared through an efficient route that proceeds in ten steps (longest linear sequence) from isobutyraldehyde. The key transformation is a multicomponent N-acylaminal construction (see scheme) that allows for late-stage fragment coupling and diversification.

Total synthesis of pederin

(Chemical Equation Presented) Blisteringly fast: The potent cytotoxic blistering agent pederin has been synthesized (see scheme). The synthesis is diastereoselective and concise (just 12 steps for the longest linear sequence), and features a formal hetero

Pederin: The metallated dihydropyran approach. Stereoselective reduction of N-acylimidates via rhodium-catalysed hydroboration

A synthesis of the insect toxin pederin (1) based upon the union of metallated dihydropyran 8 with the oxamate ester derivative 9 is described. Noteworthy features include (a) a new method for the construction of metallated dihydropyrans which tolerates h

Studies related to the synthesis of pederin. Part 2. Synthesis of pederol dibenzoate and benzoylpedamide

Syntheses of the ring B fragments (+)-pederol dibenzoate (2) and (±)-benzoylpedamide (3) of the insect toxin pederin (1) are described. An intramolecular directed aldol condensation was used to construct the tetrahydropyran ring in (+)-pederol dibenzoate

STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-PEDERINE

A mild one-pot method for the synthesis of acyclic N-(1-methoxyalkyl)amides starting from carboxylic acid and methyl imidates has been developed and applied to the first total synthesis of (+)-pederine (1), a potent insect poison.Furthermore, the stereocontrolled total synthesis of 1 was also achieved by employing acid catalyzed double alkoxy-exchange reaction of N-(1-methoxyalkyl)amide group as key step.

The Total Synthesis of (+/-)-Pederin

The conjugate addition of phenylselenomethyl-lithium to the α,β-unsaturated lactone (4) was a key step in a short synthesis of (+/-)-benzoylselenopederic acid (2); union of (2) and (+/-)-benzoylpedamide (3) by a modification of known procedures gave (+/-)-pederin (1).