158252-23-4

Upstream product

• 127943-89-9 2-hydroxy-3-cyclohexenyl-1-carboxylic acid 
• 77-78-1 dimethyl sulfate 
• 158195-43-8 acetic acid (6S)-(10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-(1R)-cyclohex-2-enyl ester 
• 159517-29-0 (1S,2R)-2-hydroxy-3-cyclohexanecarboxylic acid 

Downstream Products

• 174709-90-1 (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl (1S,2S)-2-methoxy-3-oxocyclohexanecarboxylate 
• 174709-88-7 (1S,2S)-2-methoxy-3-oxocyclohexanecarboxylic acid 
• 174709-89-8 (1S,2S)-2-methoxy-3-oxocyclohexanecarbonyl fluoride 
• 174709-87-6 (1S,2S,3R)-3-hydroxy-2-methoxycyclohexanecarboxylic acid 
• 159581-81-4 methyl (1S,2S)-3-(N-hydroxylamino)-2-methoxycyclohexane carboxylate 
• 158195-46-1 methyl (1S,2S,3R)-3-hydroxy-2-methoxy-1-cyclohexanecarboxylate 
• 159581-79-0 methyl (1S,2S)-2-methoxy-3-oxo-1-cyclohexane carboxylate 

Relevant academic research and scientific papers

Esterification via acid fluoride activation

The esterification of sterically hindered or non-nucleophilic alcohols may often be problematic. The reaction of alcohols with acid fluorides is reported to be superior to standard acid activation protocols frequently used for difficult esterifications. T

Synthetic routes to a constrained ring analog of didemnin B

The didemnin class of biologically active cyclodepsipeptides, isolated from a marine tunicate, has shown antitumor, antiviral, and immunosuppressive activities. Synthetic studies were undertaken to prepare a modified analog of one of the most potent congeners, didemnin B (1). The side chain of the isostatine unit was tethered into the macrocycle via a cyclohexane ring in order to provide a more rigid conformation and determine the importance of this unit in bioactive compounds. This modification created a new macrocycle core and generated a diastereomeric mixture of a constrained analog of didemnin B (2).

Synthetic studies of a constrained ring didemnin analog

An asymmetric Diels-Alder reaction in the presence of 3.0 M lithium perchlorate-diethyl ether was used to generate the initial stereochemistry for a cyclohexane amino acid (3), a key intermediate in the preparation of a fused ring didemnin analog. This constrained ring macrocycle should provide insight into the binding site conformation of the bioactive species.