88293-09-8

Usage

Uses

Used in Pharmaceutical Research:
1H-NAPHTHO[2,3-C]PYRAN-3-ACETIC ACID, 3,4,5,10-TETRAHYDRO-9-HYDROXY-1-METHYL-5,10-DIOXO-(1S,3R)is used as a potential candidate in pharmaceutical research for its unique molecular structure and functional groups, which may contribute to the development of new drugs or therapeutic agents.
Used in Organic Chemistry as a Synthetic Intermediate:
In the field of organic chemistry, 1H-NAPHTHO[2,3-C]PYRAN-3-ACETIC ACID, 3,4,5,10-TETRAHYDRO-9-HYDROXY-1-METHYL-5,10-DIOXO-(1S,3R)serves as a synthetic intermediate, facilitating the synthesis of more complex organic compounds or advanced pharmaceuticals.

Upstream product

• 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 

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.

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.