- An efficient synthesis of moronic and heterobetulonic acids from allobetulin
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The reaction of acetoxyallobetulin with HClO4 in refluxing Ac2O led to a mixture of diacetoxyheterobetulin (3β,28-diacetoxy-18α,19βH-urs-20-ene), diacetoxymoradiol (3β,28-diacetoxy-olean-18(19)-ene), 3β-acetoxy-21β-acetyl-20β,28-epoxy-18α,19βH-ursane, and diacetoxy-δ-erythrodiol (3β,28-diacetoxy-olean-13(18)-ene), which were isolated by column chromatography in yields of 18%, 37%, 39%, and 2%, respectively. Deacetylation of diacetoxyheterobetulin and diacetoxymoradiol followed by Jones oxidation of the corresponding triterpene 3β,28-diols led to heterobetulonic and moronic acids with overall yields of 17% and 35% from acetoxyallobetulin, respectively. The reported route makes possible the medium-to-large scale preparation of these pharmacologically important triterpenic acids.
- Khusnutdinova, El'Mira F.,Medvedeva, Natalya I.,Kazakov, Dmitri V.,Kukovinets, Olga S.,Lobov, Alexander N.,Suponitsky, Kirill Yu.,Kazakova, Oxana B.
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- Synthesis of olean-18(19)-ene derivatives from betulin
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The rare olean-18(19)-ene triterpenoids moradiol and moronic acid were synthesized from betulin, and their antiviral properties were investigated.
- Flekhter,Medvedeva,Tolstikov,Galin,Yunusov,Mai, Huong Nguen Thi,Tien, Le Viet,Savinova,Boreko,Titov,Glukhov
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- Efficient synthesis of morolic acid and related triterpenes starting from betulin
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Morolic acid (1) is a naturally occurring pentacyclic triterpene whose derivatives exhibit promising anti-HIV and other biological activities. An efficient synthesis of 1 has been accomplished in 11 steps with a total yield of 24% starting from betulin. S
- Zhang, Pu,Hao, Jia,Liu, Jun,Zhang, Luyong,Sun, Hongbin
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experimental part
p. 4304 - 4309
(2009/10/09)
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