517892-90-9

Upstream product

• 73111-01-0 4',5,7-triacetoxyflavan-4-one 
• 1070715-07-9 1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-[4-(benzyloxy)phenyl]prop-2-en-1-one 
• 345891-63-6 rac-2-[4-(benzyloxy)phenyl]-5,7-dihydroxychroman-4-one 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 517892-89-6 acetic acid 7-acetoxy-2-(4-benzyloxy-phenyl)-4-oxo-chroman-5-yl ester 

Downstream Products

• 39953-45-2 Selinondiacetat 
• 28116-98-5 rac-5,7-dihydroxy-2-[4-(3-methylbut-2-enyloxy)phenyl]chroman-4-one 

Relevant academic research and scientific papers

Simple synthesis of sakuranetin and selinone via a common intermediate, utilizing complementary regioselectivity in the deacetylation of naringenin triacetate

Sakuranetin and selinone were successfully synthesized utilizing the regioselective deacetylation of naringenin triacetate. Deacetylation of the latter at C-7 with imidazole in 1,4-dioxane at 40°C furnished the corresponding diacetate in 80% yield. Methyl

Chemo-enzymatic transformation of naturally abundant naringin to luteolin, a flavonoid with various biological effects

Luteolin [3′,4′,5,7-tetrahydroxyflavone], having multiple biological effects such as anti-inflammation, anti-allergy and anti-cancer, was prepared by chemo-enzymatic synthesis from naringin, a naturally abundant flavonoid glycoside. On the occasion of Candida antarctica lipase B (Novozym 435)-catalyzed transesterification on peracetylated form of naringin, an acetate on C-4′ was exclusively deprotected to give the key intermediate. The oxidation with 2-iodoxybenzoic acid (IBX) followed by the reductive workup provided regioselectively C-3′and C-4′ catechol functionality. After protection of the above-mentioned diol with methoxymethyl (MOM) groups and subsequent hydrolysis of all acetyl groups, a dehydrogenative introduction of double bond between C-2 and C-3 was done by the treatment with I2. Acid-catalyzed simultaneous removal of MOM groups and glycoside provided luteolin in total 8 steps and 36% overall yield from the starting material. Throughout the synthesis, diglycoside side chain effectively worked as the protective group on C-7 hydroxy group.

A simple synthesis of selinone, an antifungal component of Monotes engleri

A new synthesis of racemic 5,7-dihydroxy-2-[4-(3-methyl-but-2-enyloxy)-phenyl]chroman-4-one (selinone) (rac-1a) isolated from Monotes engleri GILG was accomplished by two routes starting from MOM-protected phloracetophenone (2).