60325-08-8

Usage

Uses

Used in Pharmaceutical Research:
(3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione is used as a subject of pharmaceutical research for its potential therapeutic properties. Its complex molecular structure and potential medicinal applications make it a promising candidate for further study.
Used in Anti-inflammatory Applications:
Furocoumarins, including (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione, have been studied for their anti-inflammatory effects. (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione may be used as an anti-inflammatory agent to help reduce inflammation and alleviate symptoms associated with various inflammatory conditions.
Used in Anti-cancer Applications:
Furocoumarins have also been studied for their anti-cancer properties. (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione may be used as an anti-cancer agent to help inhibit the growth and spread of cancer cells.
Used in Phototoxic Applications:
Furocoumarins are known for their phototoxic effects, which can be utilized in various applications. (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione may be used in phototoxic applications to target and destroy harmful cells when exposed to specific wavelengths of light.
Further research is needed to fully understand the biological activities and potential therapeutic uses of (3aS)-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione. Its complex molecular structure and potential applications make it a promising candidate for future pharmaceutical development.

Upstream product

• 107941-22-0 2-bromo-1,4,5-trimethoxynaphthalene 
• 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 
• 226213-84-9 epi-7-O-Methylkalafungin 
• 859234-21-2 (3aR,5S,11bR)-3,3a,5,11b-tetrahydro-6,7,11-trimethoxy-5-methyl-1,4-dioxacyclopent[a]anthracen-2-one 
• 859234-18-7 (4R,5R)-4-hydroxy-5-(1',4',5'-trimethoxynaphth-2'-yl)dihydrofuran-2(3H)-one 
• 859234-19-8 acetic acid 1-(1,4,5-trimethoxy-naphthalen-2-yl)-allyl ester 
• 859234-20-1 1-(1,4,5-trimethoxy-naphthalen-2-yl)-prop-2-en-1-ol 
• 859234-24-5 (3aS,5R,11bS)-6,7,11-trimethoxy-5-methyl-3,3a,5,11b-tetrahydro-2H-benzo[g]furo[3,2-c]isochromen-2-one 
• 859234-23-4 (4S,5S)-4-hydroxy-5-(1',4',5'-trimethoxynaphth-2'-yl)dihydrofuran-2(3H)-one 

Downstream Products

• 52934-83-5 4-deoxykalafunginic acid 

Relevant academic research and scientific papers

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.

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.

Unexpected regioselectivity in the synthesis of pyranonaphthoquinone via the diels-alder reaction

The unusual regioselectivity In the Diels-Alder reactions of pyranoquinone 1 with (4,4-dlmethoxybuta-1,3-dlen-2-yloxy)trimethylsilane 2 are explored by both computations and experiments. The regioselectivity Is controlled by the electrostatic interaction of the lactone ring-oxygen and the vicinal quinone oxygen on the transition structure, which can be tuned by the terminal methyl group of the butadienes.

Total synthesis of (+)-kalafungin using a tandem Michael-Dieckmann approach

A stereoselective synthesis of the antibiotic kalafungin 1 is reported. A key step involved the tandem Michael-Dieckmann reaction between methyl 2-methoxy-6-methylbenzoate 11 and the α,β-unsaturated lactone (R)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-4-methoxy-5,6-dihydropyran-2-one 10, which was prepared from (S)-aspartic acid. The C5 alkyl substituent was introduced by the use of methylmagnesium bromide and subsequent stereoselective reduction. A sequence of oxidations followed by acid-catalyzed epimerization delivered (+)-kalafungin 1.

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.

General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D

A general enantiospecific synthesis of isochromanquinones is presented.This entails an efficient synthesis of (3aS,5S,7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furopyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose.Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c.In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized.In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.

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.