151487-08-0

Basic information

• Product Name: Ampelopsin F
• Synonyms: Ampelopsin F;(5R,10S,11S,12R)-10,11-Dihydro-11,12-bis(4-hydroxyphenyl)-5,10-methano-5H-dibenzo[a,d]cycloheptene-1,3,6,8-tetrol
• CAS NO: 151487-08-0
• Molecular Formula: C28H22O6
• Molecular Weight: 454.47
• Mol File: 151487-08-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ampelopsin F(CAS DataBase Reference)
• NIST Chemistry Reference: Ampelopsin F(151487-08-0)
• EPA Substance Registry System: Ampelopsin F(151487-08-0)

Safety Data

• Hazardous Substances Data: 151487-08-0(Hazardous Substances Data)

Upstream product

• 253435-07-3 5-{6-hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-3-yl}benzene-1,3-diol 
• 1334714-28-1 C₃₂H₃₀O₆ 

Relevant articles and documents

Biosynthesis of resveratrol dimers by regioselective oxidative coupling reaction

A wide array of natural resveratrol dimers was prepared by the regioselective oxidative coupling reaction of 3,5-di-(tert-butyl)resveratrol using several types of metal oxidants (Ag2O, Ag2CO 3, MnO2, and FeCl36H2O) in different solvent systems (benzene-acetone and dichloromethane). Subsequent debutylation of these coupling products resulted in racemic pallidol and ampelosin F. Georg Thieme Verlag Stuttgart.

Total syntheses of heimiol A, hopeahainol D, and constrained analogues

IDSI to the rescue: Use of a carefully designed cascade process empowered by the unique reagent IDSI [(Et2SI)2ClaSbCl 6] provided the entire [3.2.2] bicyclic core of both targets 1 and 2 in a single, stereocontrolled operation. Use of strain energies assisted in the completion of the natural products. Copyright

Total synthesis of diverse carbogenic complexity within the resveratrol class from a common building block

Although biomimetic approaches have proven capable of converting resveratrol (1) concurrently into many of the more complex oligomers produced by plants throughout the world (such as 2-10), methods to access single members of the family have proven far more difficult to identify. Herein is described a strategy-level solution based on the use of a common building block, one distinct from Nature's starting material, that can participate in a variety of highly selective, reagent-controlled reaction cascades. These endeavors have led to the controlled synthesis of 25 natural products and analogues, molecules whose architectures encompass nearlyall the carbogenic diversity of the resveratrol family.

SYNTHESIS OF RESVERATROL-BASED NATURAL PRODUCTS

Processes for synthesizing reveratrol-based oligomers are provided. In addition, reservatrol-based oligomer compounds free of plant extract are provided.

Total synthesis of resveratrol-based natural products: A chemoselective solution

Despite the attention paid to resveratrol (1) owing to its potent biological activity, little effort has been devoted to studying resveratrol-based oligomers (such as 2-4). The first general synthetic approach is outlined for accessing the carbogenic diversity possessed by this family of compounds. (Chemical Equation Presented).

Chemical determination of the absolute structures of resveratrol dimers, ampelopsins A, B, D and F

The absolute configurations of four stilbenedimers, (+)-ampelopsins A, (+)-ampelopsins B, (-)-ampelopsins D and (+)-ampelopsins F were respectively determined on the basis of chemical evidence.