131979-99-2Relevant academic research and scientific papers
Preparation of (2R, 3R, 4R)-3-hydroxy-2,4,6-trimethylheptanoic acid via enzymatic desymmertization
Tokairin, Yoshinori,Konno, Hiroyuki
, p. 39 - 45 (2016/12/09)
Synthesis of a unique fatty acyl unit to build the N-terminus of callipeltin A and homophymine B is described. Our approach to access (2R, 3R, 4R)-3-hydroxy-2,4,6-trimethylheptanoic acid uses enzymatic hydrolysis for the desymmetrization of achiral acetate, followed by diastereoselective Roush crotylboration and Wittig olefination for the backbone construction.
Asymmetric total synthesis of (-)-rasfonin
Bhuniya, Rajib,Nanda, Samik
, p. 1153 - 1165 (2013/02/25)
An efficient chemoenzymatic asymmetric synthesis of pyranone containing natural product (-)-rasfonin is presented here. Enantioselective enzymatic desymmetrization (EED) and a unique Gluconobacter oxydans mediated oxidative kinetic resolution (OKR) have been successfully employed to install three stereocenters (C6′, C7, and C9) of the target molecule. Stereoselective Achmatowicz reaction of a properly decorated furyl nucleus led to the core pyranone structure of rasfonin. At the late stage of the synthesis Negishi coupling has been used to complete the synthesis.
Highly stereo- and regioselective synthesis of (Z)-trisubstituted alkenes via 1-bromo-1-alkyne hydroboration-migratory insertion-Zn-promoted iodinolysis and Pd-catalyzed organozinc cross-coupling
Huang, Zhihong,Negishi, Ei-Ichi
, p. 14788 - 14792 (2008/09/17)
Hydroboration of 1-bromo-1-alkynes with dibromoborane followed by addition of 3 or 4 equiv of Me2Zn provides an efficient and selective route to (Z)-2-alkenyldimethylboranes (3) or (Z)-2-alkenylmethylzincs (4), respectively, which have been suc
A formal synthesis of brassinolide
Schmittberger,Uguen
, p. 2837 - 2840 (2007/10/03)
Enzyme-catalysed differentiation of hydroxy groups in a C(2υ)-shaped tetraol-sulfide, combined with a E-stereoconvergent Ramberg-Backlund process, allowed to prepare pure (2S))-2,3-dimethyl-1-iodobutane, which could be copled with a 3,5-cyclopregnane-20-t
Enantioselective transesterification of 2-methyl-1,3-propanediol derivatives catalyzed by Pseudomonas fluorescens lipase in an organic solvent
Grisenti,Ferraboschi,Manzocchi,Santaniello
, p. 3827 - 3834 (2007/10/02)
The irreversible transesterification of racemic 2-methyl-1,3-propanediol derivatives, the monoethers 3a, 3b, 5a, and the monobenzoate 5b, with vinyl acetate catalyzed by Pseudomonas fluorescens lipase in chloroform affords enantiomerically pure chiral synthons.
An efficient chemo-enzymatic approach to the enantioselective synthesis of 2-methyl-1,3-propamedical derivatives
Santaniello, Enzo,Ferraboschi, Patrizia,Grisenti, Paride
, p. 5657 - 5660 (2007/10/02)
Lipase-catalyzed transesterification of 2-methyl-1,3-propanediol 1 in chloroform affords enantiomerically pure (S)-(-)-acetate 2, from which the (R)-(+)-silyl ethers 4a-b can be efficiently prepared (>98% ee). The (S)-TBDPS derivative 4b could be also efficiently and enantioselectively prepared by the same enzymatic procedure, starting from racemic 5b.
