134985-00-5

Basic information

• Product Name: furaquinocin E
• Synonyms: furaquinocin E;(2R)-2α,3,8-Trimethyl-3α-[(1E,3E)-4-methyl-5-hydroxy-1,3-pentadienyl]-4-hydroxy-7-methoxy-2,3,6,9-tetrahydronaphtho[1,2-b]furan-6,9-dione;(2R,3R)-2,3-Dihydro-4-hydroxy-3-[(1E,3E)-5-hydroxy-4-methyl-1,3-pentadienyl]-7-methoxy-2,3,8-trimethylnaphtho[1,2-b]furan-6,9-dione
• CAS NO: 134985-00-5
• Molecular Formula: C22H24 O6
• Molecular Weight: 384.42
• Mol File: 134985-00-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 631°Cat760mmHg
• Flash Point: 221.8°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 8.6E-17mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: furaquinocin E(CAS DataBase Reference)
• NIST Chemistry Reference: furaquinocin E(134985-00-5)
• EPA Substance Registry System: furaquinocin E(134985-00-5)

Safety Data

• Hazardous Substances Data: 134985-00-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H24O6/c1-11(10-23)7-6-8-22(4)13(3)28-21-16-14(9-15(24)17(21)22)19(26)20(27-5)12(2)18(16)25/h6-9,13,23-24H,10H2,1-5H3/b8-6+,11-7+

Upstream product

• 125224-54-6 furaquinocin B 
• 143893-04-3 C₃₆H₃₄O₉ 
• 474418-86-5 (2R,3R)-3-[(1E,3E)-(tert-butyl-dimethyl-silanyloxy)-4-methyl-penta-1,3-dienyl]-7-methoxy-2,3,8-trimethyl-4-triisopropylsilanyloxy-2,3-dihydro-naphtho[1,2-b]furan-6,9-dione 
• 143893-05-4 C₃₆H₃₂O₈ 
• 474418-84-3 4-{(2R,3R)-3-[(1E,3E)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-penta-1,3-dienyl]-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-7-yl}-4-hydroxy-2-methoxy-3-methyl-cyclobut-2-enone 
• 474418-82-1 (2R,3R)-7-bromo-3-[(1E,3E)-(tert-butyl-dimethyl-silanyloxy)-4-methyl-penta-1,3-dienyl]-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran 
• 474418-80-9 (2E,4E)-5-((2R,3R)-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydrobenzofuran-3-yl)-2-methyl-penta-2,4-dienoic acid methyl ester 
• 474418-78-5 (2R,3S)-7-bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile 
• 628299-74-1 (2R,3R)-7-Bromo-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbaldehyde 
• 474418-76-3 (2R,3S)-2,3-dimethyl-4-triisopropylsilanyloxy-2,3-dihydro-benzofuran-3-carbonitrile 
• 474418-74-1 (2R,3S)-4-hydroxy-2,3-dimethyl-2,3-dihydro-benzofuran-3-carbonitrile 
• 41046-67-7 2-iodoresorcinol 

Relevant articles and documents

Total Syntheses of Furaquinocin A, B, and E

A modular approach to the total synthesis of furaquinocins culminated in the total syntheses of furaquinocin A, B, and E. A Pd-catalyzed dynamic kinetic asymmetric transformation (DYKAT) on carbonates derived from Baylis-Hillman adducts, followed by a reductive Heck cyclization allows the enantio- and diastereoselective construction of dihydrobenzofuran 32. Introduction of a double unsatured side chain via Horner-Wadsworth-Emmons reaction and assembly of the naphthoquinone with squaric acid based methodology leads to furaquinocin E. The use of differentially substituted squaric acid derivatives allows the synthesis of three analogues of furaquinocin E. The additional stereocenters in furaquinocin A and B can be introduced with a diastereoselective Sakurai allylation. The stereoselective elongation of the side chain is possible using cross metathesis or ring closing metathesis. The obtained late-stage intermediates were successfully transformed to furaquinocin A and B.