105198-38-7Relevant articles and documents
Synthesis of aplyolide A, ichthyotoxic macrolide isolated from the skin of the marine mollusk Aplysia depilans
Spinella,Caruso,Martino,Sessa
, p. 1971 - 1973 (2001)
A convergent pathway is described for the synthesis of (S)-aplyolide A (1) using ethyl (S)-lactate as chiral source. Key steps of the synthesis are two couplings between copper(I) alkynides and propargylic halides for the formation of skipped diyne systems and were performed with an improved procedure based on the use of cesium carbonate as base for alkynide preparation.
New Acyclic Approach to 3-Amino-2,3,6-trideoxy-L-hexoses: a Stereocontrolled Synthesis of N-Benzoyl L-Daunosamine
Hirama, Masahiro,Nishizaki, Itaru,Shigemoto, Takeo,Ito, Sho
, p. 393 - 394 (1986)
N-Benzoyl L-daunosamine was synthesized stereoselectively starting from O-t-butyldimethylsilyl L-lactaldehyde and methyl propiolate; the crucial step, intramolecular conjugate addition of a carbamoyl amino group of methyl threo-5-carbamoyloxy-4-triethylsi
Enzymatic resolution of diethyl (3-hydroxy-1-butenyl) phosphonate
Attolini, Mireille,Iacazio, Gilles,Peiffer, Gilbert,Maffei, Michel
, p. 8547 - 8549 (2002)
The enzymatic esterification of diethyl (3-hydroxy-1-butenyl) phosphonate 1 with different enzymes has been carried out, and allows the preparation of (S)-1 and (R)-diethyl (3-acetoxy-1-butenyl) phosphonate 2 with very high enantiomeric excess. The absolute conguration of 1 was determined by independent synthesis from (S)-ethyl lactate.
Synergistic substrate and catalyst effects in the addition of trimethylsilyl cyanide to imines derived from lactic acid
Fields, Alexander M.,Jones, Simon
, p. 3413 - 3420 (2019)
Trimethylsilylcyanide was added to various imines derived from (2S)-ethyl lactate in the presence of Lewis acids to provide both syn- and anti- β-hydroxy-α-aminonitrile stereoisomers. Syn-products were found to be the major in most instances, however, ant
Chemoenzymatic one-pot synthesis of γ-butyrolactones
Korpak, Margarete,Pietruszka, Joerg
, p. 1420 - 1424 (2011)
The synthesis of enantio- and diastereomerically pure γ- butyrolactones is described using a one-pot, two-enzyme cascade. Ethyl 2-methyl-4-oxopent-2-enoate (2) was reduced selectively first in a 1,4-reduction using the old yellow enzyme (OYE1) [EC 1.6.99.1] and consecutively in a 1,2-reduction by an alcohol dehydrogenase [EC 1.1.1.2]. Copyright
Pd-catalyzed asymmetric intermolecular hydroalkoxylation of allene: An entry to cyclic acetals with activating group-free and flexible anomeric control
Lim, Wontaeck,Kim, Jungjoon,Rhee, Young Ho
, p. 13618 - 13621 (2014)
A ligand-directed metal-catalyzed asymmetric intermolecular hydroalkoxylation of alkoxyallene is reported. Combined with ring-closing-metathesis, this reaction offers a new atom-efficient synthetic method toward various cyclic acetals with elaborate anomeric control. Synthetic utility of the reaction was demonstrated by the atom-efficient and stereodivergent access to various mono- and disaccharides.
Studies toward the Total Synthesis of the Marine Macrolide Salarin C
Schrof, Raffael,Altmann, Karl-Heinz
, p. 7679 - 7683 (2018)
A convergent strategy for the synthesis of dideoxysalarin C (3) as a potential intermediate for the total synthesis of the marine macrolide salarin C (1) is described. The macrolactone core of 3 was assembled by Suzuki coupling between alkyl iodide 9 and
A facile approach for the synthesis of C13-C24 fragments of maltepolides A, C and D
Rao, P. Sankara,Srihari
, p. 9629 - 9638 (2016)
A linear, chiron approach for the synthesis of C13-C24 fragments of cytostatic maltepolides A, C and D consisting of a tetrahydrofuran subunit and a chiral alkenyl/alkyl substituent is achieved from (+)-diethyl l-tartrate. The other chiral stereocenters were generated by employing key reactions such as Crimmins aldol, alkynylation and CeCl3·7H2O mediated Luche reduction reactions.
PYRAZOLO[3,4-B]PYRAZINE SHP2 PHOSPHATASE INHIBITORS
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Page/Page column 127, (2021/02/26)
The invention provides new pyrazine derivatives of formula (I): or a tautomer or a solvate or a pharmaceutically acceptable salt thereof, wherein the substituents are as defined herein. The invention also provides pharmaceutical compositions comprising sa
A Unified Strategy for the Asymmetric Synthesis of Highly Substituted 1,2-Amino Alcohols Leading to Highly Substituted Bisoxazoline Ligands
Shrestha, Bijay,Rose, Brennan T.,Olen, Casey L.,Roth, Aaron,Kwong, Adon C.,Wang, Yang,Denmark, Scott E.
, p. 3490 - 3534 (2021/02/16)
A general procedure for the asymmetric synthesis of highly substituted 1,2-amino alcohols in high yield and diastereoselectivity is described that uses organometallic additions of a wide range of nucleophiles to tert-butylsulfinimines as the key step. The addition of organolithium reagents to these imines follows a modified Davis model. The diastereoselectivity for this reaction depends significantly on both the nucleophile and electrophile. These highly substituted 1,2-amino alcohols are used to synthesize stereochemically diverse and structurally novel, polysubstituted 2,2′-methylene(bisoxazoline) ligands in high yields.
