116060-83-4

Upstream product

• 14618-80-5 (R)-benzyl glycidol 
• 159213-03-3 N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide 
• 2930-05-4 (S)-benzyl glycidyl ether 
• 802294-64-0 propionic acid 

Downstream Products

• 1005508-22-4 C₁₆H₂₄O₃ 
• 1005508-23-5 C₁₆H₂₄O₃ 
• 388082-11-9 (E)-(4S,6R)-7-Benzyloxy-1-{(2R,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-6-triethylsilanyloxy-hept-1-en-3-ol 
• 388082-03-9 (E)-(4S,6R)-7-Benzyloxy-1-{(2R,3R)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-6-triethylsilanyloxy-hept-1-en-3-one 
• 388082-04-0 (E)-(2R,4S)-1-Benzyloxy-7-{(2R,3R)-3-[(S)-3-hydroxy-4-(4-methoxy-benzyloxy)-butyl]-2-methyl-oxiranyl}-4-methyl-hept-6-ene-2,5-diol 
• 388082-10-8 (E)-(4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-hept-1-en-3-one 
• 388082-06-2 (4S,6R)-7-Benzyloxy-6-hydroxy-1-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-heptan-3-one 
• 388082-05-1 (E)-(2R,4S)-1-Benzyloxy-7-[(2S,3R,6S)-3-hydroxy-6-(4-methoxy-benzyloxymethyl)-2-methyl-tetrahydro-pyran-2-yl]-4-methyl-hept-6-ene-2,5-diol 
• 388081-99-0 ((3S,5R)-6-Benzyloxy-3-methyl-2-oxo-5-triethylsilanyloxy-hexyl)-phosphonic acid dimethyl ester 

Relevant academic research and scientific papers

Lituarine synthetic studies. An efficient, stereocontrolled construction of the common c(7-19) tricyclic spiroketal fragment.

A highly efficient, stereocontrolled synthesis of (+)-4, the common C(7-19) tricyclic spiroketal fragment of the lituarines A, B, and C (1-3), has been achieved. Highlights of the synthesis include a remarkably facile 6-endo cyclization to access the C(8-

Practical syntheses of enantiomerically enriched γ-lactones and γ-hydroxy ketones by the alkylation of pseudoephedrine amides with epoxides and their derivatives

Pseudoephedrine amide enolates are shown to undergo efficient alkylation reactions with epoxides as electrophiles. Reactions with monosubstituted epoxides are subject to stereochemical matching such that the pairing leading to the 1,3-syn diastereomer is a highly selective, synthetically useful process, while the pairing forming the 1,3-anti diastereomer is not. Reactions with the 1,1-disubstituted epoxide isobutylene oxide are also highly diastereoselective and synthetically useful, but ethylene oxide exhibits poor diastereoselectivity. As an alternative to the use of ethylene oxide, 2-(tert-butyldimethylsilyloxy)ethyl iodide is shown to undergo highly diastereoselective and efficient alkylation reactions with pseudoephedrine amide enolates. Interestingly, epoxides and alkyl halides are found to attack opposite π-faces of pseudoephedrine amide enolates. The products of each of these alkylation reactions are transformed efficiently into γ-lactones by acidic hydrolysis and into methyl ketones by the addition of methyllithium. The methodology described provides useful procedures for the synthesis of enantiomerically enriched γ-lactones and γ-hydroxy ketones.

STEREOSELECTIVE KINETIC PROTONATION OF CHIRAL γ-LACTONE ENOLATES

When lithium enolates generated from five chiral α,γ-disubstituted γ-lactones are treated with proton sources, formation of the α,γ-syn epimers always predominates over the α,γ-anti epimers in ratios of 10.2-2.9:1.Higher syn/anti ratios are obtained via silyl enolates in some cases.Chirality discrimination by chiral proton source is also observed in particular cases.