258283-82-8

Upstream product

• 64490-45-5 2-iodo-3,4,5-trimethoxybenzyl alcohol 
• 18173-64-3 tert-butyldimethylsilanol 
• 75921-68-5 1,2,3-trimethoxy-5-(methoxymethyl)benzene 
• 3840-31-1 (3,4,5-trimethoxyphenyl)methanol 
• 6178-44-5 ethyl 3,4,5-trimethoxybenzoate 
• 258283-81-7 6-(6-hydroxymethyl-2,3,4-trimethoxy-phenyl)-benzo[1,3]dioxole-5-carbaldehyde 
• 94838-88-7 2-formyl-4,5-(methylenedioxy)benzeneboronic acid 

Downstream Products

• 258283-80-6 6-[2,3,4-trimethoxy-6-(2-oxo-2,5-dihydro-furan-3-ylmethyl)-phenyl]-benzo[1,3]dioxole-5-carbaldehyde 

Relevant academic research and scientific papers

A concise atroposelective formal synthesis of (-)-steganone

We describe herein the atroposelective formal synthesis of (-)-steganone, a parent member of Steganotaenia araliacea dibenzocyclooctadiene lignan lactones. Our synthesis features an atropodiastereoselective biaryl Suzuki-Miyaura cross-coupling reaction with de up to 99% using as a chiral auxiliary an enantiopure and efficiently converted β-hydroxy sulfoxide derivative. A highly atroposelective formal synthesis of (-)-steganone is described highlighting the use of an enantiopure sulfoxide as a chiral auxiliary in the Suzuki-Miyaura cross-coupling reaction.

Total Synthesis of (-)-Steganone Utilizing a Samarium(II) Iodide Promoted 8-Endo Ketyl-Olefin Cyclization

A six-step synthesis of (±)-steganone from commercially available 3,4,5-trimethoxybenzyl alcohol features a samarium(II) iodide promoted 8-endo ketyl-olefin coupling to install, in a single transformation, the 8,5 ring system common to the lignan lactones. The racemic synthesis provided the basis for the construction of (-)-steganone, which exploited a chromium tricarbonyl moiety both to establish and protect the desired absolute stereochemistry through key transformations, including a SmI2-promoted 8-endo radical cyclization and two palladium-catalyzed couplings.