56922-59-9

Upstream product

• 1159796-00-5 C₉H₁₄O₆S 
• 183626-27-9 (3aS,7aS)-3a-hydroxy-3,3a,7,7a-tetrahydrobenzofuran-6(2H)-one 
• 1133797-34-8 4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-hydroxycyclohexa-2,5-dien-1-one 
• 897025-80-8 4-[2-hydroxyethyl]-4-hydroperoxy-2,5-cyclohexadien-1-one 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 40661-45-8 cornoside 

Relevant academic research and scientific papers

Total synthesis of incargranine A

Synthetic studies into the origins of the alkaloid incargranine A have resulted in the development of a four-step (longest linear sequence) total synthesis. This synthesis has been scaled-up to provide gram-scale quantities of material, which would alternatively require extraction of several metric-tons of dried-whole Chinese Trumpet-Creeper plants (Incarvillea mairei var. grandiflora).

ISOLATION OF CORNOSIDE FROM OLEA EUROPAEA AND ITS TRANSFORMATION INTO HALLERIDONE

Olea europaea contains, besides oleuropein, demethyloleuropein, verbascoside and ligstroside, cornoside which can be easily transformed into halleridone.Key Word Index - Olea europea; Oleaceae; oleuropein; cornoside; halleridone; secoiridoid.

Total synthesis of incarvilleatone and incarviditone: Insight into their biosynthetic pathways and structure determination

A concise biomimetic total synthesis of incarvilleatone and incarviditone is achieved in one pot via the highly stereoselective hetero-and homodimerization of (±)-rengyolone, respectively. The structure of incarviditone is revised on the basis of spectroscopic and computational evidence.

Tandem sequence of phenol oxidation and intramolecular addition as a method in building heterocycles

A tandem phenol oxidation-Michael addition furnishing oxo- and -aza-heterocycles has been developed. Dirhodium caprolactamate [Rh 2(cap)4] catalyzed oxidation by T-HYDRO of phenols with alcohols, ketones, amides, carboxylic acids, and N-Boc protected amines tethered to their 4-position afforded 4-(tert-butylperoxy)cyclohexa-2,5-dienones that undergo Bronsted acid catalyzed intramolecular Michael addition in one-pot to produce oxo- and -aza-heterocycles in moderate to good yields. The scope of the developed methodology includes dipeptides Boc-Tyr-Gly-OEt and Boc-Tyr-Phe-Me and provides a pathway for understanding the possible transformations arising from oxidative stress of tyrosine residues. A novel method of selective cleavage of O-O bond in hindered internal peroxide using TiCl4 has been discovered in efforts directed to the construction of cleroindicin F, whose synthesis was completed in 50% yield over just 3 steps from tyrosol using the developed methodology.

Enantioselective total synthesis of all of the known chiral cleroindicins (C-F): Clarification among optical rotations and assignments

(Chemical Equation Presented) Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural pro

Oxidative de-aromatization of para-alkyl phenols into para-peroxyquinols and para-quinols mediated by oxone as a source of singlet oxygen

(Chemical Equation Presented) Easy does it: Easily handled and environmentally safe oxone generates singlet oxygen which effects the simple and selective oxidative de-aromatization of para-alkyl phenols 1 into para-peroxyquinols 2 under very mild conditions with good to excellent yields. A one-pot access to para-quinols 3 from 1 is also possible after treatment of the crude reaction mixture with sodium thiosulfate.

BIOGENESIS-LIKE TRANSFORMATION OF SALIDROSIDE TO RENGYOL AND ITS RELATED CYCLOHEXYLETANOIDS OF FORSYTHIA SUSPENSA

Photooxygenation of salidroside (8) in methanol in presence of Rose Bengal afforded cornoside (9), which, on high pressure hydrogenation with 5percent palladium on activated carbon, yielded rengyoside B (6).Reduction of 6 with sodium borohydride gave rengyoside A(5) stereoselectively.By enzymatic hydrolysis, 9, 6 and 5 furnished rengyolone (4), rengyoxide (3) and rengyol (1), respectively. Similerly, p-hydroxyphenylethanol (10), the aglycone part of salidroside (8), was oxygenated photochemically to a dienone alcohol, which cyclized spontaneously to rengyolone (4).Hallerone (17) was obtained by the photooxygenation of p-hydroxyphenylethyl acetate (10b).Thus the plausible biosynthetic routes from salidroside (8) to rengyol (1) and the related natural cyclohexylethanoids were simulated chemically.