Asymmetric Synthesis and Sensory Evaluation of Sedanenolide

Modulatory Effect of Guinep (Melicoccus bijugatus Jacq) Fruit Pulp Extract on Isoproterenol-Induced Myocardial Damage in Rats. Identification of Major Metabolites Using High Resolution UHPLC Q-Orbitrap Mass Spectrometry

“…Peak 17 was identified as the lactone sedanenolide (C 12 H 12 O 2 − ) [22] and Peak 18 was assigned to the sesquiterpene valerenic acid (C 15 H 21 O 2 − ) [23]. Peak 15, with a [M − H] − ion at m / z : 221.15488, was identified as the antifungic norsesquiterpene alcohol rishitin (C 14 H 22 O 2 − )[24].…”

From Seeds ofApium graveolensLinn. to a Cerebral Ischemia Medicine: The Long Journey of 3-n-Butylphthalide

“…Duan and co-workers prepared ( S )-NBP in a three-step process, in 66% overall yield, starting from methyl 2-formylbenzoate, after aldol-lactonization reaction with n -butanone, using (2 R )- N -((2 R )-1-hydroxy-4-methyl-1-phenyl-1-(l2-phosphaneyl)­pentan-2-yl)­pyrrolidine-2-carboxamide, to give enantiomerically pure ( S )-3-(2-oxobutyl)­isobenzofuran-1­(3 H )-one ( 14 ) (Figure ), followed by thioacetalization and desulfurization. Oguro and Watanabe described the synthesis and sensory evaluation of ( RS )- , ( R )- , and ( S )-NBP prepared by intramolecular Diels–Alder reaction of racemic or enantiomerically pure 1-ethynylpentyl 2,4-pentadienoate ( 15 ) (Figure ) as the minor compound in a mixture where the major component was sedanenolide, a phthalide natural product, isolated in 1977 from the essential oil of celery .…”

“…Oguro and Watanabe described the synthesis and sensory evaluation of ( RS )- , ( R )- , and ( S )-NBP prepared by intramolecular Diels–Alder reaction of racemic or enantiomerically pure 1-ethynylpentyl 2,4-pentadienoate ( 15 ) (Figure ) as the minor compound in a mixture where the major component was sedanenolide, a phthalide natural product, isolated in 1977 from the essential oil of celery . Ghorai and co-workers described the organocatalyzed intramolecular oxa-Michael reaction of in situ formed peroxy hemiacetals, as an efficient method for the synthesis of chiral lactones, that was applied to the formal total synthesis of ( R )-NBP .…”

“…42 (S)-NBP was found to be superior to (R)-NBP in odor and sensory properties. 41 Ghorai and co-workers 43 described the organocatalyzed intramolecular oxa-Michael reaction of in situ formed peroxy hemiacetals, as an efficient method for the synthesis of chiral lactones, that was applied to the formal total synthesis of (R)-NBP. The reaction of (E)-2-(3-oxobut-1-en-1-yl)benzaldehyde ( 16) (Figure 4) with TBHP, in the presence of 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5vinylbicyclo[2.2.2]octan-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione as catalyst, gave (R)-3-(2-oxobutyl)isobenzofuran-1(3H)-one in 58% yield that could be eventually transformed into (R)-NBP.…”