111060-73-2Relevant academic research and scientific papers
Enantiodivergent biosynthesis of the dimeric sphingolipid oceanapiside from the marine sponge Oceanapia phillipensis. Determination of remote stereochemistry
Nicholas, Gillian M.,Molinski, Tadeusz F.
, p. 4011 - 4019 (2007/10/03)
The absolute stereochemistry of oceanapiside, an antifungal α,ω-bis- aminohydroxylipid with four stereogenic centers from the marine sponge Oceanapia phillipensis Dendy, 1895, has been obtained as 2S,3R,26R,27R from development and application of a general CD method based on superposition of additive exciton couplings in perbenzoyl derivatives of bis-amino alcohols. The method allows simultaneous determination of the local relative configuration at each of the termini of the long chain bis-aminolipid and also relates the absolute configuration of the two remote termini. Oceanapiside contains erythro and threo relative configurations at C1,2 and C26,27, respectively, but opposite absolute configurations at the amino substituted carbons C2 and C27 which implies an enantiodivergent biogenesis formally derived from both D- and L-amino acids.
Zinc-Mediated Allylation of N-Protected α-Amino Aldehydes in Aqueous Solution. Stereoselective Synthesis of Anti- and Syn-β-Amino Alcohols with Functionalized Allyl Groups
Hanessian, Stephen,Park, Haeil,Yang, Rui-Yang
, p. 353 - 354 (2007/10/03)
Anti-β-amino alcohols with differently substituted allyl groups were obtained in high chemical yields and in good to excellent diastereoselectivities via Zn-mediated allylation of 2-(dibenzyl-amino)aldehydes in aqueous media. Swern oxidation, and reduction with NaBH4 gave enantiopure syn-β-amino alcohols in good yields.
Diastereoselection during 1,2-Addition of the Allylindium Reagent to α-Thia and α-Amino Aldehydes in Aqueous and Organic Solvents
Paquette, Leo A.,Mitzel, Thomas M.,Isaac, Methvin B.,Crasto, Curtis F.,Schomer, William W.
, p. 4293 - 4301 (2007/10/03)
The stereochemistry of the indium-promoted reaction of allyl bromide with α-thia (PhS and MeS), disubstituted α-amino (Bn2N, Me2N, isoindolyl), and protected α-amino aldehydes (Ac and Boc) in water has been evaluated. The reactions involving the sulfur derivatives are minimally diastereoselective, indicating that the allylindium reagent is not thiophilic. Chelation is not observed and π-facial discrimination is achieved via Felkin - Ahn transition states under the steric control of the substituents. The Garner aldehyde is also anti-diastereoselective. Interestingly, N-acetylmannosamine is appreciably responsive to chelation control and is capable of generating 90% of the syn β-amino alcohol when reacted in a 0.5 M NH4Cl solution. While the α-dibenzylamino substituent is too bulky to enter into complexation, the α-dimethylamino group is not and can lead to high levels (99%) of syn diastereomer. The size of other neighboring substituents does have an impact on π-facial discrimination in these systems and can erode the stereoselectivity accordingly.
