124070-58-2

Upstream product

• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 98-88-4 benzoyl chloride 
• 85909-02-0 N-benzyl-N-(tert-butoxycarbonyl)-benzamide 
• 65-85-0 benzoic acid 
• 5949-05-3 (S)-Citronellal 

Downstream Products

• 1228447-67-3 (S)-5-formyl-3-methylpentyl benzoate 

Relevant academic research and scientific papers

Direct Hydrofluorination of Methallyl Alkenes Using a Methanesulfonic Acid/Triethylamine Trihydrofluoride Combination

The use of a methanesulfonic acid/triethylamine trihydrofluoride combination for the direct hydrofluorination of methallyl-containing substrates is reported. Under those metal-free conditions that use readily available, cheap, and easy to handle reagents,

Synthesis and biological analysis of truncated calyculone H

Herein, we report for the first time the design and linear synthesis of a truncated calyculone H (7) that lacks the telltale isopropyl/isopropylene groups, whereas the 12-membered macrocycle remains intact. Key steps for the framework of target molecule include allylic oxidation using SeO2, Sharpless asymmetric epoxidation, Barbier zinc allylation, and ring-closing metathesis (RCM) reactions. A second truncated “calyculone-like” analogue, 27, with a different oxidation pattern around the ring was also synthesized following a similar strategy. Screening for in vitro cytotoxicity against a panel of 60 human cancer cell lines revealed that 7 was as potent if not more so (for a few cell lines) than the natural product calyculone A (2).

Enantiospecific Synthesis of Nepetalactones by One-Step Oxidative NHC Catalysis

An efficient oxidative NHC-catalyzed one-step transformation of (S)-or (R)-8-oxocitronellal to nepetalactone (NL) in enantio- A nd diastereomerically pure form has been developed. Several new and "easy to make" N-Mes-or N-Dipp-substituted 1,2,4-triazolium salts carrying nitroaromatic groups on N1 were synthesized and evaluated as precatalysts in combination with base and stoichiometric organic oxidant. Under optimized conditions, NLs are accessible in very good yields and diastereomerically pure under mild conditions. The oxidant used could be recovered and recycled under operationally simple conditions.

Cesium Carbonate Catalyzed Esterification of N-Benzyl- N-Boc-amides under Ambient Conditions

We report a general activated amide to ester transformation catalyzed by Cs2CO3. Using this approach, esterification proceeds under relatively mild conditions and without the need for a transition metal catalyst. This method exhibits broad substrate scope and represents a practical alternative to existing esterification strategies. The synthetic utility of this protocol is demonstrated via the facile synthesis of crown ether derivatives and the late-stage modification of a representative natural product and several sugars in reasonable yields.

Synthesis of acyclic ketones by catalytic, bidirectional homologation of formaldehyde with nonstabilized diazoalkanes. Application of a chiral diazomethyl(pyrrolidine) in total syntheses of erythroxylon alkaloids

This work offers a catalytic approach to convergent ketone assembly based upon formal and tandem C-H insertion of diazoalkanes in the presence of limiting amounts of monomeric formaldehyde, which is easily generated as a gas by thermolysis of the inexpensive and abundant paraformaldehyde (～30 USD/kg). The method forms di-, tri-, and even tetrasubstituted acetones with high efficiency, and it has streamlined a synthesis of (-)-dihydrocuscohygrine in which the absolute stereochemistry of a proline-based starting material is preserved. Assisted by the advent of new protocols for hydrazone oxidation, we also provide full details on handling non-carbonyl-stabilized diazo compounds.

Enhancement of antiproliferative activity by molecular simplification of catalpol

Two iridoid scaffolds were synthesized enantioselectively using as key step an l-proline-catalyzed α-formyl oxidation. The in vitro antiproliferative activities were evaluated against a representative panel of human solid tumor cell lines. Both iridoids induced considerably growth inhibition in the range 0.38-1.86 μM. Cell cycle studies for these compounds showed the induction of cell cycle arrest at the G1 phase. This result was consistent with a decrease in the expression of cyclin D1. Damaged cells underwent apoptosis as indicated by specific Annexin V staining.