26121-57-3

Upstream product

• 26121-56-2 nigakilactone I 
• 30315-04-9 (-)-picrasin B acetate 
• 26121-56-2 picrasin B 
• 123834-73-1 1β,11β-diacetoxy-20-((phenoxythiocarbonyl)oxy)-16-methoxy-9β-picrasan-12-one 
• 123857-39-6 1β,11β-diacetoxy-16β-methoxy-9β-picrasan-12-one 
• 123834-84-4 1β,11β-diacetoxy-16α-methoxy-9β-picrasan-12-one 
• 123834-87-7 (-)-2-bromo-2-deoxypicrasin 
• 123834-86-6 (+)-2-deoxypicrasin B 
• 123834-85-5 12,16α-dimethoxypicras-12-en-1,11-dione 
• 123834-66-2 12-hydroxy-16α-methoxypicras-12-en-1,11-dione 
• 127897-11-4 (3aR,5R,6aR,7aS,8R,11aS,11bS,11cS)-5-Hydroxy-2-methoxy-3,8,11a,11c-tetramethyl-3a,4,5,6a,7,7a,8,9,10,11a,11b,11c-dodecahydro-6-oxa-benzo[de]anthracene-1,11-dione 
• 123834-65-1 1β,11β-dihydroxy-16α-methoxy-9β-picrasan-12-one 
• 26121-56-2 (+)-picrasin B 
• 83543-82-2 picrasinoside-A 

Downstream Products

• 26121-56-2 nigakilactone I 
• 30315-04-9 Acetic acid (3aR,6aR,7aS,8R,10S,11aS,11bS,11cS)-2-methoxy-3,8,11a,11c-tetramethyl-1,5,11-trioxo-1,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-10-yl ester 
• 26121-56-2 (+)-picrasin B 
• 30315-04-9 (-)-picrasin B acetate 
• 76-78-8 quassin 
• 210623-98-6 Benzoic acid (3aR,6aR,7aS,8S,11aS,11bS,11cS)-2-methoxy-3,8,11a,11c-tetramethyl-1,5,11-trioxo-1,3a,4,5,6a,7,7a,8,11,11a,11b,11c-dodecahydro-6-oxa-benzo[de]anthracen-10-yl ester 
• 76-78-8 quassin 

Relevant academic research and scientific papers

Semisynthetic derivatives of quassin

The natural product quassin has been modified in order to produce compounds with potential antimalarial action. The modifications include demethylation, reduction of the keto function, esterification with simple organic acids and - to enhance the uptake through the biological barriers and increase the stability of the compounds - with lipoamino acids.

A Partial Synthesis of (-)-Shinjulactone H from (+)-Quassin

A partial synthesis of (-)-shinjulactone H (3) from (+)-quassin (1) required the selective manipulation of two similar O-methyldiosphenol groups.Protection of the δ-lactone in 1 as an ortho ester, selective reduction of the C-1 carbonyl group, hydrolysis of the resulting enol ether in the A ring, and catalytic hydrogenation of the O-methyldiosphenol in the C ring delivered an intermediate possessing an α-ketol group in the A ring and an α-methoxy ketone group in the C ring.Demethylation and concomitant α-ketol tautomerization in the A ring delivered (-)-shinjulactone H (3).

An Enantioselective Synthesis of (+)-Picrasin B, (+)-Δ2-Picrasin B, and (+)-Quassin from the R-(-) Enantiomer of the Wieland-Miescher Ketone

An enantioselective total synthesis of (+)-picrasin B (1), (+)-Δ2-picrasin B (11), and (+)-quassin (12) from the R-(-) enantiomer of the Wieland-Miescher ketone (3) employed an A-AB-ABC-ABCD sequence to assemble the tetracyclic skeleton.The cru

A PARTIAL SYNTHESIS OF PICRASIN B AND Δ2-PICRASIN B1

The regioselective reductive demethylation of the O-methyldiosphenol functionality in the A ring of quassin (3) with chlorotrimethylsilane and sodium iodide furnished picrasin B (1).Swern oxidation of 1 furnished Δ2-picrasin B (2), and O-methylation of 2 regenerated quassin (3).

PICRANOSIDE-A, A NOVEL QUASSINOID GLUCOSIDE FROM PICRASMA AILANTHOIDES PLANCHON

A novel quassinoid glucoside picrasinoside-A was isolated from Picrasma ailanthoides PLANCHON and the structure was established from spectral data, chemical transformations into picrasin B and quassin, and enzyme hydrolysis.The aglycon picrasin B showed a significant clastogenic activity in cell cultures of Don lung cells of Chinese hamster.

QUASSINOIDS. ISOLATION FROM SOULAMEA MUELLERI AND STRUCTURES OF 1,12-DI-O-ACETYL SOULAMEANONE AND Δ2-PICRASIN B. X-RAY ANALYSIS OF SOULAMEANONE

The structures of soulameanone, 1,12-di-O-acetyl soulameanone and Δ2-Picrasin B, new quassinoids from Soulamea muelleri (Simaroubaceae), were determined by spectrometric methods and chemical correlation, and that of Soulameanone confirmed by single crystal X-ray analysis.