104499-08-3Relevant articles and documents
Chelation-Controlled Chemo-, Regio- and Enantio-Selective Synthesis of Homoallylic Alcohols
Calo, Vincenzo,Fiandanese, Vito,Nacci, Angelo,Scilimati, Antonio
, p. 7283 - 7292 (1994)
Optically active allylic sulphides 10-13, bearing two different leaving groups, react with organocopper reagents by selective substitution of the heterocyclic moiety leading to optically active homoallylic pivalates with chemo-, regio- and enantio-control.This selectivity seems to be related to the coordination exerted by the heterocyclic nucleus towards the organometal.
Total synthesis of the epidermal growth factor inhibitor (-)-reveromycin B
Cuzzupe,Hutton,Lilly,Mann,McRae,Zammit,Rizzacasa
, p. 2382 - 2393 (2001)
The total synthesis of the epidermal growth factor inhibitor reveromycin B (2) in 25 linear steps from chiral methylene pyran 13 is described. The key steps involved an inverse electron demand hetero-Diels-Alder reaction between dienophile 13 and diene 12 to construct the 6,6-spiroketal 11 which upon oxidation with dimethyldioxirane and acid catalyzed rearrangement gave the 5,6-spiroketal aldehyde 9. Lithium acetylide addition followed by oxidation/reduction and protective group manipulation provided the reveromycin B spiroketal core 8 which was converted into the reveromycin A (1) derivative 6 in order to confirm the stereochemistry of the spiroketal segment. Introduction of the C1-C10 side chain began with sequential Wittig reactions to form the C8-C9 and C7-C6 bonds, and a tin mediated asymmetric aldol reaction installed the C4 and C5 stereocenters. The final key steps to the target molecule 2 involved a Stille coupling to introduce the C21-C22 bond, succinoylation, selective deprotection, oxidation, and Wittig condensation to form the final C2-C3 bond. Deprotection was effected by TBAF in DMF to afford reveromycin B (2) in 72% yield.
Synthesis, X-ray analysis, and biological activities of novel oxazolidinethiones
Saygili, Nezire,?zalp, Meral,Yildirim, Leyla Tatar
, p. 1264 - 1269 (2015)
Oxazolidinethione compounds were synthesized starting from racemic and enantiopure β-amino alcohols. The molecular structure of oxazolidinethione 6a was elucidated by single-crystal x-ray crystallography. Oxazolidinethione compounds screened for antimicro
N-(diazoacetyl)oxazolidin-2-thiones as sulfur-donor reagents: Asymmetric synthesis of thiiranes from aldehydes
Cano, Israel,G?mez-Bengoa, Enrique,Landa, Aitor,Maestro, Miguel,Mielgo, Antonia,Olaizola, Iurre,Oiarbide, Mikel,Palomo, Claudio
supporting information, p. 10856 - 10860 (2013/01/15)
Sulfur tyranny: Thiiranes, instead of oxiranes, can be obtained in a highly stereoselective manner through the cycloaddition reaction of N-acyl oxazolidine tethered diazo thione compounds with aldehydes catalyzed by RhII. Thus, this reaction provides versatile adducts S functionalized at both the α and β position, with concomitant generation of two contiguous stereocenters. Copyright
