107495-44-3

Upstream product

• 33524-31-1 2,5-dimethoxybenzyl alcohol 
• 60732-17-4 2,5-dimethoxybenzyl bromide 

Downstream Products

• 1430737-38-4 (1R,3aR,4S,7aR)-4-(2,5-dimethoxybenzyl)-1-hydroxy-4,7a-dimethylhexahydro-1H-inden-5(6H)-one 
• 107495-45-4 (2S,4S)-2-tert-Butyl-4-(2,5-dimethoxybenzyl)-5-oxo-1,3-dioxolan-4-essigsaeure 

Relevant academic research and scientific papers

Enantioselective Total Synthesis and Structural Revision of Dysiherbol A

A 12-step total synthesis of the natural product dysiherbol A, a strongly anti-inflammatory and anti-tumor avarane meroterpene isolated from the marine sponge Dysidea sp., was elaborated. As key steps, the synthesis features an enantioselective Cu-catalyzed 1,4-addition/enolate-trapping opening move, an Au-catalyzed double cyclization to build up the tetracyclic core-carbon skeleton, and a late installation of the C5-bridgehead methyl group via proton-induced cyclopropane opening associated with spontaneous cyclic ether formation. The obtained pentacyclic compound (corresponding to an anhydride of the originally suggested structure for dysiherbol A) showed identical spectroscopic data as the natural product, but an opposite molecular rotation. CD-spectroscopic measurements finally confirmed that both the constitution and the absolute configuration of the originally proposed structure of (+)-dysiherbol A need to be revised.

Promotion of Appel-type reactions by N-heterocyclic carbenes

N-Heterocyclic carbenes (NHCs) have been extensively used as a versatile class of catalysts and ligands in organocatalytic and organometallic chemistry. However, there are only a small number of synthetic applications where they act as reagents. Here we demonstrate that NHCs can be used as stoichiometric redox reagents for Appel-type halogenation reactions of alcohols. This new reactivity reveals a fresh and interesting aspect and enriches the chemistry of NHCs in an underexplored area. The potential of performing this chemical transformation at the catalytic level using an NHC-oxide derivative is also investigated.

Diastereoselective synthesis of complex cis-hexahydroindanes by reductive alkylation

An efficient and operationally simple approach to complex cis-hexahydroindanes is reported. Upon Birch reduction of unprotected, C4-alkylated tetrahydroindanols and electrophilic trapping of the tetrasubstituted enolate, cis-fused products are formed with a new stereogenic quaternary carbon. The reaction is convergent, completely diastereoselective, and shows a broad scope with regard to the electrophile.

Synthetic Anthracyclinones, XXXIV. - An Enantiomerically Pure AB Building Block for a Daunomycinone Synthesis via Incorporation of (S)-Malic Acid

(S)-Malic acid (1) is incorporated via the dilithium salt 4 of the acetal 3 into the fully functionalized daunomycinone building block 24 without loss of enantiomeric purity.