471-56-7

Upstream product

• 559-74-0 friedelin 
• 113376-15-1 friedel-3-en-3-yl benzoate 
• 287110-78-5 3-[(1S,2S,4aS,4bR,6aR,10aR,10bS,12aR)-2-((R)-1-Hydroxy-ethyl)-2,4b,6a,9,9,10b,12a-heptamethyl-octadecahydro-chrysen-1-yl]-propionic acid 
• 64-19-7 acetic acid 
• 113376-12-8 4α-hydroxyfriedelan-3-one 
• 29621-75-8 3,4-secofriedelan-3 <*> 4-olide 
• 161739-60-2 3-trimethylsiloxyfriedel-3-ene 

Downstream Products

• 6938-93-8 A-nor-friedelene-⁽²⁾ 
• 29621-75-8 3,4-secofriedelan-3 <*> 4-olide 

Relevant academic research and scientific papers

Hemisynthetic secofriedelane triterpenes with inhibitory activity against the growth of human tumor cell lines in vitro

Seco acids 7 and 9 and hydroxylated analogues 5 and 6 derived from friedelane triterpenes were synthesized stereoselectively in high yields. Compounds 5-9 were evaluated for their ability to inhibit in vitro the growth of three human tumor cell lines, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), and SF-268 (CNS cancer). Only compounds 7 and 9 were found to possess significant growth inhibitory effects, exhibiting GI 50 values that range from 24.6 to 32.8 μM and 10.9 to 17.6 μM, respectively.

Studies on triterpenoids: Conversion of friedelanones into some secofriedelanes

Baeyer-Villiger oxidation of friedelin (1), cerin (3), its acetate (4) and canophyllol (7) with m-chloroperbenzoic acid yields friedelolactone (2), 2α-hydroxyfriedelolactone (5), 2α-acetoxyfriedelolactone (6) and apetalactone (8), respectively.However, 3α-hydroxyfriedelan-2-one (12) and its acetate (13) give a 2,3:3,4-disecofriedelane (14) under similar conditions.The formate ester so produced affords a methyl ester (15) upon treatment with diazomethane while basic hydrolysis and acidification leads to a nor-δ-lactone (16).Sodium borohydride reduction of friedelolactone, 2α-hydroxyfriedelolactone and the nor-δ-lactone leads to reductive opening of the lactone ring.CrO3/py oxidation of 3,4-secofriedelan-3,4-diol (17), produced from friedelolactone, yields 3,4-secofriedelan-3-ol-4-one (23).Basic hydrolysis of friedelolactone gives a hydroxy acid (25) which undergoes CrO3/py oxidation to a 4-oxo-compound (28).The latter (28) forms a methyl ester (29) and also undergoes Baeyer-Villiger oxidation to an acetate (30) which on hydrolysis affords another nor-δ-lactone (31).

Basic Autoxidation of Friedelin

Base-catalized autoxidation of a triterpene ketone, friedelin, in the presence of potassium t-butoxide gave four products, and their structures and formation mechanism were investigated.The common intermediate to these compounds was suggested to be 4-hydroperoxyfriedelan-3-one, not friedelane-2,3-dione. 3-Oxafriedel-1-ene-2-carboxylic acid was a dehydration product of the main product, 2-hydroxy-3-oxafriedelane-2-carboxylic acid.