353248-28-9

Upstream product

• 757249-30-2 1-[(1R,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(toluene-4-sulfonyl)-7-oxa-2-aza-bicyclo[4.1.0]hept-1-yl]-cyclopentanol 
• 353248-25-6 (+)-1-[(5S)-5-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-1,4,5,6-tetrahydropyridin-2-yl]cyclopentanol 
• 353248-27-8 (-)-(1R,4S,7S)-4-(tert-butyldimethylsilanyloxy)-2-(toluene-4-sulfonyl)-1-(1-trimethylsilanyloxycyclopentyl)-7-oxa-2-azabicyclo[4.1.0]heptane 

Downstream Products

• 634891-84-2 (-)-(3S,5S,6R)-methanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-oxo-1-(toluene-4-sulfonyl)-1-azaspiro[5.5]undec-5-yl ester 
• 634891-85-3 (+)-(3S,6R)-3-(tert-butyldimethylsilanyloxy)-1-(toluene-4-sulfonyl)-1-azaspiro[5.5]undec-4-en-7-one 

Relevant academic research and scientific papers

An asymmetric formal synthesis of fasicularin

An asymmetric formal synthesis of fasicularin (1) is described. This natural product, isolated from the extracts of the marine invertebrate Nephteis fasicularis, has shown modest cytotoxicity towards Vero cells. Fasicularin is among only two members of th

Investigations of α-siloxy-epoxide ring expansions forming 1-azaspirocyclic ketones

The construction of 1-azaspirocyclic cycloalkanones using a siloxy-epoxide semipinacol ring expansion process was examined. Functionalized l-azaspiro[5.5]undecan-7-ones (1-azaspirocyclic cyclohexanones) proceeded in high chemical yields with complete diastereoselectivity using titanium tetrachloride as the Lewis acid promoter. The formation of functionalized 6-azaspiro[5.4]-decan-1-ones (1-azaspirocyclic cyclopentanones) proceeded in high chemical yield with little diastereoselectivity. Modification of reaction parameters such as the Lewis acid promoter or the nature of the silyl ether allowed for the preferential formation of either ("anti" or "syn" 1,2 alkyl shift) diastereomeric product. An explanation for the different reactivity profiles between the cyclobutanol silyl ethers and cyclopentanol silyl ethers is provided.

A Formal Construction of Fasicularin

(Equation presented) Our synthetic approach toward fasicularin is presented. Key steps in this construction are a siloxy-epoxide semipinacol rearrangement, a B-alkyl Suzuki reaction and an intramolecular SN2 reaction.