1443256-45-8Relevant articles and documents
Stereoselective total synthesis of phenolic nonadecanediol
Chinnababu, Baggu,Purushotham Reddy, Sudina,Venkatesham, Kunuru,Chandra Rao, Dasireddi,Venkateswarlu, Yenamandra
, p. 613 - 618 (2014/06/09)
A simple and highly efficient synthetic route has been developed for synthesis of 1-(4-hydroxyphenyl)nonadecane-3,5-diol (1). The two stereogenic centers were generated by employing proline asymmetric α-hydroxylation (MacMillan α-hydroxylation), Jacobsen's hydrolytic kinetic resolution (HKR), and, finally, Yamaguchi oxirane opening as key steps (Scheme 2). Copyright
Synthesis and configuration of the phenolic nonadecanediol isolated from the resinous exudates of heliotropium sinuatum
Chen, Chao-Yuan,Zhang, Shao-Min,Wu, Yikang,Gao, Po
, p. 348 - 355 (2013/02/26)
The (3S,5R) and (3R,5R) isomers of the title compound were synthesized from enantiopure epoxide chiral building blocks readily accessible from D-gluconolactone. The former (a syn-1,3-diol) gave 1H and 13C NMR spectroscopic data and optical rotation in good agreement with those reported for the natural product, whereas distinct differences were found with the data for the latter (an anti-1,3-diol). These results unambiguously showed that the absolute configuration of the natural product must be (3S,5R).