81381-68-2

Usage

InChI:InChI=1/C40H38O10/c1-20(2)4-9-26-32(44)14-12-28(38(26)48)40(50)36-29(25-10-8-24(42)19-35(25)47)16-21(3)17-30(36)37-33(45)15-11-27(39(37)49)31(43)13-6-22-5-7-23(41)18-34(22)46/h4-8,10-15,17-19,29-30,36,41-42,44-49H,9,16H2,1-3H3/b13-6+/t29-,30-,36-/m0/s1

Upstream product

• 870-63-3 prenyl bromide 
• 165606-47-3 2',4',2,4‐tetrahydroxy‐3‐(3‐menthyl‐2‐butenyl)chalcone 
• 13709-06-3 2,4-bis(methoxymethoxy)benzaldehyde 
• 65490-08-6 2-hydroxy-4-(methoxymethoxy)acetophenone 
• 112756-05-5 <2-13C>cinnamic acid 

Relevant academic research and scientific papers

Chiral Boron Complex-Promoted Asymmetric Diels-Alder Cycloaddition and Its Application in Natural Product Synthesis

An efficient method for the asymmetric Diels-Alder cycloaddition of 2'-hydroxychalcones with acyclic or cyclic dienes has been successfully developed. The Diels-Alder cycloaddition is mediated by a chiral boron complex with VANOL, affording the corresponding products in high yields and with excellent diastereo- and enantioselectivities. This reaction enabled the enantioselective construction of cyclohexene skeletons crucial for the total synthesis of a number of Diels-Alder-type natural products (-)-nicolaioidesin C, (-)-panduratine A, (-)-kuwanon I, (+)-kuwanon J, and (-)-brosimones A and B.

Enantioselective biomimetic total syntheses of kuwanons i and J and brosimones A and B

The first enantioselective total syntheses of prenylflavonoid Diels-Alder natural products (-)-kuwanonI, (+)-kuwanonJ, (-)-brosimoneA, and (-)-brosimoneB have been accomplished from a common intermediate based on a concise synthetic strategy. Key elements of the synthesis include a biosynthesis-inspired asymmetric Diels-Alder cycloaddition mediated by a chiral ligand/boron Lewis acid, as well as a process involving regioselective Schenck ene reaction, reduction, and dehydration to realize a biomimetic dehydrogenation for generation of the required diene precursor. Furthermore, a remarkable tandem inter-/intramolecular asymmetric Diels-Alder cycloaddition process was applied for the synthesis of (-)-brosimoneA. Four in a row: The first enantioselective total syntheses of the prenylflavonoid natural products (-)-kuwanonI, (+)-kuwanonJ, (-)-brosimoneA, and (-)-brosimoneB have been accomplished based on a concise synthetic strategy. Key elements of the synthesis include a biosynthesis-inspired asymmetric Diels-Alder cycloaddition mediated by a chiral ligand/boron Lewis acid, as well as a process involving regioselective Schenck ene reaction, reduction, and dehydration.

Dual p-coumaroyl CoA biosynthesis in Morus alba cell cultures

Morus alba callus and cell suspension cultures specifically produce chalcomoracin (1) and kuwanon J (2) both originated from cinnamoylpolyketide intermediate. Administration of [2-13C]cinnamic acid N-acetylcysteamine thioester to the M. alba ce