171868-02-3Relevant academic research and scientific papers
Synthesis of a 35-member stereoisomer library of bistramide A: Evaluation of effects on actin state, cell cycle and tumor cell growth
Wrona, Iwona E.,Lowe, Jason T.,Turbyville, Thomas J.,Johnson, Tanya R.,Beignet, Julien,Beutler, John A.,Panek, James S.
scheme or table, p. 1897 - 1916 (2009/07/01)
Synthesis and preliminary biological evaluation of a 35-member library of bistramide A stereoisomers are reported. All eight stereoisomers of the C1-C13 tetrahydropyran fragment of the molecule were prepared utilizing crotylsilane reagents 9 and 10 in our
[4 + 2]-Annulations of chiral organosilanes: Application to the total synthesis of leucascandrolide A
Su, Qibin,Dakin, Les A.,Panek, James S.
, p. 2 - 24 (2007/10/03)
Complete details of an asymmetric synthesis of leucascandrolide A (1) are described. The synthesis highlights the use of two diastereoselective [4 + 2]-annulations for the assembly of the functionalized bispyranyl macrolide 3. An efficient assembly and un
A convenient multigram synthesis of highly enantioenriched methyl 3-silylglycidates
Lowe, Jason T.,Youngsaye, Willmen,Panek, James S.
, p. 3639 - 3642 (2007/10/03)
A multigram scale synthesis of the four stereoisomers of methyl 3-silylglycidates (epoxysilanes) with high enantiopurity is described. Key reactions include a Sharpless asymmetric epoxidation (SAE) of a trans-vinylsilane and an enzymatic resolution of a r
A route to enantiomerically-enriched α-silyl aldehydes from 2,3-epoxy alcohols
Chauret, Denise C.,Chong, J. Michael,Ye, Qing
, p. 3601 - 3614 (2007/10/03)
Asymmetric epoxidation of (E)-3-trialkylsilyl-2-propen-1-ols gives the expected epoxides with high enantioselectivity. Ring opening reactions of these epoxides with organocopper reagents furnishes 1,2-diols which are readily cleaved with Pb(OAc)4 to afford α-silyl aldehydes with no detectable loss of stereochemistry.
Stereocontrolled synthesis of α-trialkylsilyl-β,γ-unsaturated aldehydes via palladium (0) catalysis synthetic usefulness
Le Bideau,Gilloir,Nilsson,Aubert,Malacria
, p. 7487 - 7510 (2007/10/03)
The reaction of silicon substituted vinyloxiranes in the presence of catalytic amount of palladium (0) catalyst affords the title compounds. This new reaction proceeds smoothly, under very mild conditions and with complete chirality transfer. One-pot addition of selected organometallic nucleophiles to these aldehydes at very low temperature led to a highly selective preparation of the corresponding alcohols in very good yields. Influence of substituents on the silicon atom and of the ligands of palladium have been studied.
Optically active acylsilanes. Synthesis of selected 2,3-O-isopropylidene-1-(trialkyl/arylsilyl)glyceraldehyde derivatives
Raubo,Wicha
, p. 577 - 586 (2007/10/02)
Syntheses of 1-trimethylsilyl-, 1-tert-butyldimethylsilyl, 1-dimethylphenylsilyl- and 1-triphenylsilyl-2,3-O-isopropylideneglyceraldehyde derivatives, 6a, 6b, 6c, and 6d, respectively, is described.
