68930-68-7

Basic information

• Product Name: frenolicin B
• Synonyms: frenolicin B;(1R)-1β-Propyl-3,4,5,10-tetrahydro-4α,9-dihydroxy-5,10-dioxo-1H-naphtho[2,3-c]pyran-3α-acetic acid 3,4-lactone;(3aR)-3,3aα,5,11bα-Tetrahydro-7-hydroxy-5α-propyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione;3,3aα,5,11bα-Tetrahydro-7-hydroxy-5α-propyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione
• CAS NO: 68930-68-7
• Molecular Formula: C18H16O6
• Molecular Weight: 328.31604
• Mol File: 68930-68-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 622°C at 760 mmHg
• Flash Point: 232.7°C
• Appearance: /
• Density: 1.46g/cm³
• Vapor Pressure: 4.6E-16mmHg at 25°C
• Refractive Index: 1.639
• CAS DataBase Reference: frenolicin B(CAS DataBase Reference)
• NIST Chemistry Reference: frenolicin B(68930-68-7)
• EPA Substance Registry System: frenolicin B(68930-68-7)

Safety Data

• Hazardous Substances Data: 68930-68-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H16O6/c1-2-4-10-14-15(18-11(23-10)7-12(20)24-18)16(21)8-5-3-6-9(19)13(8)17(14)22/h3,5-6,10-11,18-19H,2,4,7H2,1H3/t10-,11-,18+/m1/s1

Upstream product

• 187862-09-5 (S)-4-[1-(tert-Butyl-dimethyl-silanyloxy)-4,5-dimethoxy-naphthalen-2-yl]-3-hydroxy-butyric acid tert-butyl ester 
• 187862-11-9 (S)-3-Hydroxy-4-(5-methoxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-butyric acid tert-butyl ester 
• 10023-13-9 Desoxyfrenolicin-methylester 
• 10023-11-7 Deoxyfrenolicin 
• 73804-48-5 trans-methyl <9-hydroxy-1-propyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-naphtho<2,3-c>pyran-3-yl>acetate 
• 77363-69-0 (E)-4-[(3aR,4S,5S,6S)-6-Hydroxy-4-((S)-1-hydroxy-butyl)-2,2-dimethyl-3a,4,5,6-tetrahydro-naphtho[1,8-de][1,3]dioxin-5-yl]-but-2-enoic acid methyl ester 
• 73794-57-7 ((7R,7aR,9S,11R,11aR,11bS)-7-Hydroxy-2,2-dimethyl-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracen-9-yl)-acetic acid methyl ester 
• 73794-58-8 ((7aS,9R,11S,11aS,11bR)-2,2-Dimethyl-7-oxo-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracen-9-yl)-acetic acid methyl ester 
• 73794-56-6 (7S,7aS,9R,11S,11aS,11bR)-2,2-Dimethyl-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracene-7,9-diol 
• 73804-49-6 (+/-)-deoxyfrenolicin 
• 54419-64-6 1-(2,5-dimethoxyphenyl) butan-1-one 
• 216358-09-7 (3aR,5S,11bR)-3,3a,5,11b-tetrahydro-7-methoxy-5-propyl-1,4-dioxacyclopent[a]anthracen-2,6,11-trione 
• 1404583-65-8 (3aR,5S,11bR)-3,3a,5,11b-tetrahydro-7-methoxy-5-propyl-1,4-dioxacyclopent[a]anthracen-2,6,11-trione 
• 149083-04-5 (R)-<2,5-Dimethoxy-6-((R)-1-hydroxy-2-propenyl)phenyl>propylcarbinol 

Relevant articles and documents

A diastereoselective oxa-pictet-spengler-based strategy for (+)-frenolicin B and epi -(+)-frenolicin B synthesis

An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.

A chiron approach to the total synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin

A general, efficient, and common strategy for the synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin is reported here. The strategy involves the synthesis of a key building block alkyne from a cheap chiral pool material, d-glucono-δ-lactone, Doetz benzannulation, oxa-Pictet-Spengler reaction, and H2SO 4-mediated epimerization.

Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions

Frenolicin B, an anticoccidial agent, has been synthesizes in six steps from ketone 3.Racemic kalafungin, an antifungal agent, has been synthesized in five steps.The key step in both syntheses, a regioselective Diels-Alder reaction, proceeds with complete