333796-77-3Relevant articles and documents
Enantioselective synthesis of flavan-3-ols using a mitsunobu cyclization
Krohn, Karsten,Ahmed, Ishtiaq,John, Markus
experimental part, p. 779 - 786 (2009/09/06)
The synthesis of four flavan-3-ols with different substitution patterns and electron densities has been achieved in high stereo- and regioselectivity by a one-step Mitsunobu reaction from the corresponding diols, which were prepared by enantioselective Sharpless dihydroxylation of suitable olefins. The six-membered flavan-3-ols were the only cyclization products and the theoretically possible formation of five-membered rings during the Mitsunobu cyclization was not observed. The flavanols are important starting materials for the synthesis of dimers such as the procyanidins or other coupling products such as the flavan part of the potent DNA polymerase β inhibitor myristinin A. The enantioselectivities of both the Sharpless dihydroxylation and the Mitsunobu cyclization steps were monitored by chiral HPLC. Georg Thieme Verlag Stuttgart New York.
Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents
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, (2008/06/13)
Novel compounds are useful as chemotherapeutic, chemopreventative, and antiangiogenic agents are provided. The compounds are flavanoids, including flavanones, flavanols, and chalcones. The compounds have the structure of formula (I) 1wherein R1 through R3 and R5 through R11 are defined herein, and α, β, and γ are optional bonds, providing that when α is absent, β is present, and when β is absent, α is present. When α is present, preferred R4 moieties are selected from O, S, NH and CH2, and when α is absent, preferred R4 groups are selected from OH, SH, NH2 and CH3. When γ is present, the preferred R5 substituent is O, while when γ is absent, the preferred R5 substituent is OH. Pharmaceutical compositions are provided as well, as are methods of synthesis and use.
Synthesis of a 3,4,5-trimethoxybenzoyl ester analogue of epigallocatechin-3-gallate (EGCG): A potential route to the natural product green tea catechin, EGCG
Zaveri, Nurulain T.
, p. 843 - 845 (2007/10/03)
matrix presented The synthesis of a trimethoxybenzoyl ester (D-ring) analogue of epigallocatechin-3-gallate (EGCG) is described. The versatile synthesis route can be used to synthesize A, B, and D ring analogues of EGCG and involves a key cyclization of t