11048-15-0

Basic information

• Product Name: Kalafungin
• Synonyms: Kalafungin;NSC 137443;3,3aα,5,11bα-Tetrahydro-7-hydroxy-5α-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione;Kalamycin;U-19718;(3AS,5S,11bS)-7-Hydroxy-5-methyl-3aH-benzo[g][1,3]-dioxolo[4,5-c]isochromene-2,6,11(5H,11bH)-trio
• CAS NO: 11048-15-0
• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 302.237
• Mol File: 11048-15-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 624.5°Cat760mmHg
• Flash Point: 240.8°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.667
• CAS DataBase Reference: Kalafungin(CAS DataBase Reference)
• NIST Chemistry Reference: Kalafungin(11048-15-0)
• EPA Substance Registry System: Kalafungin(11048-15-0)

Safety Data

• Hazardous Substances Data: 11048-15-0(Hazardous Substances Data)

Usage

Uses

Antifungal.

InChI:InChI=1/C16H12O6/c1-6-11-13(16-9(21-6)5-10(18)22-16)14(19)7-3-2-4-8(17)12(7)15(11)20/h2-4,6,9,16-17H,5H2,1H3/t6-,9-,16+/m1/s1

Upstream product

• 226213-84-9 epi-7-O-Methylkalafungin 
• 81418-42-0 3-acetyl-5-methoxy-1,4-naphthoquinone 
• 86823-79-2 1,4,8-trimethoxy-2-acetyl-3-(5-tert-butoxy-2-furyl)naphthalene 
• 86823-80-5 1,4,8-trimethoxy-2-(1-hydroxyethyl)-3-(5-tert-butoxy-2-furyl)naphthalene 
• 83662-31-1 2-acetyl-8-methoxy-1,4-dihydroxynaphthalene 
• 73318-26-0 7-methoxy-3-(phenylthio)-1(3H)-isobenzofuranone 
• 28281-58-5 7-methoxyisobenzofuran-1(3H)-one 
• 23125-83-9 9-O-methylkalafungin 
• 1001438-91-0 (1S,3S)-3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran-3-acetic acid 
• 88293-09-8 (1S,3S)-3,4,5,10-tetrahydro-9-hydroxy-3-(2-hydroxyethyl)-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran 
• 1001438-89-6 (1S,3S)-3,4,5,10-tetrahydro-3-(2-hydroxyethyl)-9-methoxy-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran 
• 1001438-86-3 (R)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-5,6-dihydro-4-methoxy-2H-pyran-2-one 
• 79383-44-1 methyl 2-methyl-6-methoxybenzoate 
• 1001438-87-4 (S)-3,4-dihydro-10-hydroxy-3-(2-(tert-butyldimethylsilyloxy)ethyl)-9-methoxy-1H-naphtho[2,3-c]pyran-1-one 

Downstream Products

• 52934-83-5 4-deoxykalafunginic acid 

Relevant articles and documents

Efficient synthesis of (+)-kalafungin and (-)-nanaomycin D by asymmetric dihydroxylation, oxa-pictet-spengler cyclization, and H2SO 4-mediated isomerization

The pyranonaphthoquinone antibiotics and antitumor agents (+)-kalafungin (1) and (-)-nanaomycin D (3 = ent-1) were synthesized from 1,5-napthalenediol (13) in 11 steps. Stereocontrol was high: 99.5 ee/93% diastereoselectivity for 1, 98.5% ee/94% diastereoselectivity for 3. Enantiocontrol was achieved by the asymmetric dihydroxylation of the β,γ-unsaturated ester 9. Diastereocontrol was realized in the final step by an almost complete epimerization in H2SO4.

The divergent asymmetric synthesis of kalafungin, 5-epi-frenolicin B and related pyranonaphthoquinone antibiotics

A divergent, asymmetric method for the synthesis of pyranonaphthoquinones is reported. The synthetic strategy applies a Staunton-Weinreb annulation between substituted ortho-toluates and the (R)-pyran-2-one 7 to construct the key naphthopyranone intermediates. Stereoselective introduction of either a methyl or propyl C5 alkyl substituent by use of Grignard addition/silane- mediated reduction and a sequence of oxidations gave a series of pyranonaphthoquinones including kalafungin 1, 5-epi-9-methoxykalafungin 34 and 5-epi-frenolicin B 24.

Enantiodivergent total syntheses of nanaomycins and their enantiomers, kalafungins

The first, enantiospecific total syntheses of pyranonaphthoquinone antibiotics, nanaomycins D and A, and their enantiomers kalafungin and 4-deoxykalafunginic acid, are described by an 'enantiodivergent' strategy from a common optically active intermediate, (1S,3RS,4S)-3,4-dihydro-5,9,10-trimethoxy-1-methyl-1H-naphtho[2,3-c]pyr an-3,4-diol, which has been derived from L-rhamnose via condensation of 4-methoxy-3-(phenylsulfonyl)-1-(3H)-isobenzofuranone and methyl 3,4,6-trideoxy-α-L-glycero-hex-3-enopyranosid-2-ulose.