125665-10-3

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 125664-95-1 N-propionyl-(2R)-bornane-(10,2)-sultam 
• 100-52-7 benzaldehyde 
• 556837-26-4 (1S,5R,7R)-4-[(Z)-1-(tert-Butyl-dimethyl-silanyloxy)-propenyl]-10,10-dimethyl-3-thia-4-aza-tricyclo[5.2.1.0^1,5]decane 3,3-dioxide 
• 125760-70-5 (2S,3R)-1-((6R)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-3-hydroxy-2-methyl-3-phenylpropan-1-one 

Downstream Products

• 125760-70-5 (2S,3R)-1-((6R)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-3-hydroxy-2-methyl-3-phenylpropan-1-one 
• 25201-44-9 (1R,2R)-2-methyl-1-phenylbut-3-en-1-ol 
• 94199-26-5 (2S,3R)-methyl 3-hydroxy-2-methyl-3-phenylpropionate 

Relevant academic research and scientific papers

Stereodivergent total synthesis of Br-nannocystins underpinning the polyketide (10R,11S) configuration as a key determinant of potency

Continuing our investigation into the structure-activity relationship of antiproliferative macrocyclic nannocystins, we describe herein total synthesis of all four stereoisomers of Br-nannocystins as well as a simplified analogue varying at the polyketide C10 and C11 positions. Biological evaluation of these compounds against PANC1 cancer cell lines showed that both the (10R,11S) configuration and its associated two substituents are crucial for high potency.

Enantiomerically pure, crystalline 'anti'-aldols from N-acylbornanesultams: Aldolization and structure of intermediate t-butyldimethylsilyl-N,O-ketene acetal

O-Silylation of N-propionylsultam 1 provides pure Z O-silyl-N,O-ketene acetal 2 which undergoes Lewis acid promoted addition of aromatic and aliphatic aldehydes to give diastereomerically pure, crystalline "anti" aldols 7 or their silylethers 3. Hydroperoxide-assisted hydrolysis/esterification of products 7 yields enantiomerically pure methoxycarbonyl aldols (11, 12, 13, 14).