22268-16-2

Usage

Uses

Altersolanol A is a tetrahydroanthraquinone with phytotoxic and antibacterial activity.

InChI:InChI=1/C16H16O8/c1-16(23)14(21)10-9(13(20)15(16)22)12(19)8-6(11(10)18)3-5(24-2)4-7(8)17/h3-4,13-15,17,20-23H,1-2H3/t13-,14+,15+,16-/m0/s1

Upstream product

• 119644-07-4 alterporriol D 
• 65120-69-6 3-chloro-5-hydroxy-7-methoxy-1,4-naphthoquinone 
• 116889-06-6 (1RS,2RS,3SR,4SR)-3,4-epoxy-1,2,3,4-tetrahydro-2,5-dihydroxy-7-methoxy-2-methyl-1-(trimethylsiloxy)-9,10-anthraquinone 
• 70063-61-5 5-hydroxy-7-methoxy-1,4-naphthoquinone 
• 116888-93-8 5-acetoxy-7-methoxy-1,4-naphthoquinone 
• 116889-01-1 (1RS,2RS)-1,2-dihydro-2,5-dihydroxy-7-methoxy-2-methyl-1-(trimethylsiloxy)-9,10-anthraquinone 
• 116888-97-2 (1RS,2RS,3RS,4aRS,9aRS)-5-acetoxy-2,3-epoxy-1,2,3,4,4a,9a-hexahydro-7-methoxy-2-methyl-1-(trimethylsiloxy)-9,10-anthraquinone 
• 116888-94-9 (1RS,4aRS,9aRS)-5-acetoxy-1,4,4a,9a-tetrahydro-7-methoxy-1-(trimethylsiloxy)-9,10-anthraquinone 

Relevant academic research and scientific papers

First enantioselective total synthesis of altersolanol A

The first enantioselective total synthesis of altersolanol A, a secondary metabolite from the endophytic fungi Stemphylium globuliferum and Alternaria solani, is described. The key step towards the tetrahydroanthraquinone core was an asymmetric Diels-Alder (D-A) cycloaddition promoted by (R)-3,3′-diphenyl-BINOL/boron Lewis acid with good to excellent yields and excellent diastereo- and enantioselectivity (>95 : 5 dr and 98 : 2 er).

Alterporriol D and E, Modified Bianthraquinones from Alternaria porri (Ellis) Ciferri

A culture liquid of Alternaria porri afforded novel bianthraquinones named alterporriol D and E, whose structures were determined by spectroscopic methods as well as by degradation to the known compound.Alterporriol D and E were found to be atropisomers of each other.

rac-Altersolanol A and Related Tetrahydroanthraquinones, Total Synthesis and Cytotoxic Properties

A key step in the first synthesis of racemic altersolanol A (1a) is the regioselective Diels-Alder reaction of 5-acetoxy-7-methoxy-1,4-naphthoquinone (12) with 2-methyl-1-(trimethylsiloxy)-1,3-butadiene (13) to afford the adduct 14.The structure of 14 has been confirmed by X-ray measurements.The hydroxy groups of ring A are introduced by epoxidation of 14 to 20, rearrangement to the allylic alcohol 26, epoxidation to 31, and opening of the oxirane to rac-altersolanol A (1a).Similar products were obtained starting from juglone (15).Many of the intermediate epoxidesand also compounds 42-44 show remarkable cytotoxicity in cell cultures but all compounds were too toxic to be useful as anticancer agents.

ALTERPORRIOL C: A MODIFIED BIANTHRAQUINONE FROM ALTERNARIA PORRI

The spent growth medium and mycelia of Alternaria porri afforded a novel anthraquinone named alterporriol C, whose structure was determined by spectroscopic methods as well as by degradation to known compounds.Alterporriol C was found to be an α,β'-bianthraquinone derived from macrosporin and altersolanol A.Key Word Index - Alternaria porri; α,β'-bianthraquinone; alterporriol C.