215171-11-2Relevant articles and documents
Asymmetric synthesis of ES-285, an anticancer agent isolated from marine sources
Allepuz, Ana C.,Badorrey, Ramon,Diaz-de-Viliegas, Maria D.,Galvez, Jose A.
experimental part, p. 6172 - 6178 (2010/03/26)
The asymmetric synthesis of (2S,3R)-2-amino-3-octane-decanol hydrochloride (ES-285-HC1) was achieved in eight steps in ca. 38% overall yield from the N-benzylimine-derived from. (R)-2,3-O-isopropylidene glyceraldehyde, which is easily available on gram sc
Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O- isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine
Merino, Pedro,Castillo, Elena,Franco, Santiago,Merchan, Francisco L.,Tejero, Tomas
, p. 12301 - 12322 (2007/10/03)
A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2- O-isopropylidene-D-glyceraldehyde. The obtained α,β-dialkoxy hydroxylamines can serve as starting points for the synthesis of both aminodiols and α- hydroxy-β-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer.
Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols
Merino, Pedro,Castillo, Elena,Merchan, Francisco L.,Tejero, Tomas
, p. 1725 - 1729 (2007/10/03)
The stereoselective addition of Grignard reagents to α-alkoxy nitrones has been achieved with excellent stereocontrol using ZnBr2 and Et2AlCl as precomplexing agents to obtain the corresponding syn- and anti- adducts, respectively. The obtained hydroxylamines have been transformed into valuable 3-amino-1,2-diols.
An enantioselective, stereodivergent approach to anti- and syn-α-hydroxy-β-amino acids from anti-3-amino-1,2-diols. Synthesis of the ready for coupling Taxotere side chain
Pasto, Mireia,Moyano, Albert,Pericas, Miquel A.,Riera, Antoni
, p. 243 - 262 (2007/10/03)
Both anti- and syn-α-hydroxy-β-amino acids are efficiently synthesised in protected form and high enantiomeric purity from readily available anti-N-Boc-1-tert-butyldimethylsilyl-3-amino-1,2-diols. The preparation of the anti series is straightforward, and
A convenient, stereodivergent approach to the enantioselective synthesis of N-Boc-aminoalkyl epoxides
Castejon, Patricia
, p. 3019 - 3022 (2007/10/02)
An efficient, stereodivergent and enantioselective synthesis of N-Boc-aminoalkyl epoxides has been developed. Starting from enantiomerically enriched anti N-diphenylmethyl-3-amino-1,2-diols, and after a change in the nitrogen protecting group, an intramol
Enantioselective Synthesis of Fully Protected anti 3-Amino-2-Hydroxy Butyrates
Pasto, Mireia,Moyano, Albert,Pericas, Miquel A.,Riera, Antoni
, p. 2329 - 2342 (2007/10/03)
An efficient enantioselective synthesis of fully protected anti 3-amino-2-hydroxybutyrates has been developed.Starting from enantiomerically enriched anti N-diphenylmethyl-3-amino-1,2-butanediol, after a change in the nitrogen protecting group, the primary alcohol was protected by regioselective reduction of the corresponding p-methoxybenzylidene acetal.Formation of the oxazolidine and deprotection of the primary alcohol followed by oxidation afforded protected α-hydroxy-β-amino acids in good yield.Since the source of asymmetry is a catalytic Sharpless epoxidation, both enantiomeric series are available and the methodology developed here is expected to be of broad applicability.
A short enantioselective synthesis of N-Boc-α-amino acids from epoxy alcohols
Poch, Marta
, p. 7781 - 7784 (2007/10/02)
A new and efficient enantioselective synthesis of Boc-α-amino acids has been developed. Starting from an enantiomerically enriched epoxy alcohol the sequence involves a regioselective nucleophilic epoxide opening by diphenylmethylamine (benzhydrilamine), hydrogenolysis/ protection of the amino group, and oxidation of the diol moiety.
