31087-58-8Relevant articles and documents
(±)-Diinsininone: made nature's way
Selenski, Carolyn,Pettus, Thomas R.R.
, p. 5298 - 5307 (2007/10/03)
We report the synthesis of diinsininone (33), the aglycone of (±)-diinsinin (2). Thereby, we complete the first construction of a proanthocyanidin (PA) type-A compound incorporating a [3.3.1]-bicyclic ketal as its characteristic core. Our strategy utilizes a coupling between a benzopyrilium salt and a flavanone that proves applicable to other PA type-A compounds. During this undertaking, treatment of naringenin (9) with 2-iodoxybenzoic acid (IBX) followed by reductive work-up affords eriodictyol (10). This reactivity mirrors that of catechol hydroxylase (F3H) found in the flavonoid pathway. Other interesting transformations include the formation of flavonoids through an ortho-quinone methide (o-QM) cycloaddition-oxidation sequence and regioselective β-glycosidations of several unprotected flavanones suggesting a likely synthesis of 2 from the aglycone 33.
Chiral molecular recognition on formation of a metalloanthocyanin: A supramolecular metal complex pigment from blue flowers of salvia patens
Kondo, Tadao,Oyama, Kin-Ichi,Yoshida, Kumi
, p. 894 - 897 (2007/10/03)
Most blue flower color is the result of a metalloanthocyanin, a stoichiometric self-assembled supramolecular pigment consisting of six molecules of an anthocyanin, six molecules of an anthocyanin, six molecules of flavone, and two metal atoms. We have iso