1392476-32-2

Usage

Uses

Used in Pharmaceutical Industry:
(3R,4aS,10bR)-4a,5,6,10b-Tetrahydro-3-(4-hydroxy-3-methoxyphenyl)-9-methoxy-3H-naphtho[2,1-b]pyran-8-ol is used as a potential therapeutic agent for the treatment of various diseases due to its biological activities, such as antioxidant and anti-inflammatory properties.
Used in Cosmetic Industry:
(3R,4aS,10bR)-4a,5,6,10b-Tetrahydro-3-(4-hydroxy-3-methoxyphenyl)-9-methoxy-3H-naphtho[2,1-b]pyran-8-ol is used as an ingredient in cosmetic products for its potential antioxidant and anti-inflammatory properties, which may help protect and soothe the skin.
Used in Research:
(3R,4aS,10bR)-4a,5,6,10b-Tetrahydro-3-(4-hydroxy-3-methoxyphenyl)-9-methoxy-3H-naphtho[2,1-b]pyran-8-ol is used as a research compound to study its biological effects and potential applications in various fields, such as medicine, pharmaceuticals, and cosmetics.

Upstream product

• 179260-96-9 4-methoxy-3-(triisopropylsilyloxy)-benzaldehyde 

Relevant academic research and scientific papers

Highly trans-Selective Arylation of Achmatowicz Rearrangement Products by Reductive γ-Deoxygenation and Heck-Matsuda Reaction: Asymmetric Total Synthesis of (-)-Musellarins A-C and Their Analogues

Fully functionalized pyranuloses derived from Achmatowicz rearrangement (AR) are versatile building blocks in organic synthesis. However, access to trans-2,6-dihydropyrans from pyranuloses remains underexplored. Herein, we report a new two-step trans arylation of AR products to access 2,6-trans-dihydropyranones. This new trans-arylation method built on numerous plausible, but unsuccessful, direct arylation reactions, including Ferrier-type and Tsuji-Trost-type reactions, was finally enabled by an unprecedented, highly regioselective γ-deoxygenation of AR products by using Zn/HOAc and a diastereoselective Heck-Matsuda coupling. The synthetic utility of the reaction was demonstrated in the first asymmetric total synthesis of (-)-musellarins A-C and 12 analogues in 11-12 steps. The brevity and efficiency of our synthetic route permitted preparation of enantiomerically pure musellarins and analogues (>20 mg) for preliminary cytotoxicity evaluation, which led us to identify two analogues with three-to-six times greater potency than the musellarins as promising new leads. O leaves, Ar comes: A highly regio- and diastereoselective trans-arylation of Achmatowicz rearrangement products by an unprecedented Zn-mediated reductive γ-deoxygenation and Heck-Matsuda reaction was developed for the efficient synthesis of trans-2-aryl-6-alkyl dihydropyranones (see scheme: L.A.=Lewis acid). The synthetic utility of this new method was further demonstrated in the first asymmetric total synthesis of (-)-musellarins A-C and 12 analogues in 11-12 steps.

Total syntheses of (±)-musellarins A-C

The first, diastereoselective total syntheses of musellarins A-C were achieved concisely with 7.8-9.8% yields in 15-16 steps. The key synthetic features include (i) an Achmatowicz rearrangement, Kishi reduction, and Friedel-Crafts cyclization to construct