Concise synthesis of rodgersinol and determination of the C-10 absolute configuration.
Rodgersinol was synthesized via seven linear steps in 31% overall yield, and the absolute configuration of the C-10 stereogenic center was elucidated. The key feature of the synthesis involves the efficient Cu(II)-mediated coupling of two aromatic moieties for the diaryl ether intermediate and the enantioselective construction of the hydroxypropyl substituent by a regio- and stereoselective methyl addition to the chiral aryloxiranes in an inversion manner.
Seo
Seung-Yong
SY
College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Jung
Jong-Wha
JW
Jung
Jae-Kyung
JK
Kim
Nam-Jung
NJ
Chin
Young-Won
YW
Kim
Jinwoong
J
Suh
Young-Ger
YG
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D031995:Saxifragaceae / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D010636:Phenols; C518115:rodgersinol