149715-93-5Relevant articles and documents
First enantioselective total synthesis of altersolanol A
Mechsner, Bastian,Hen?en, Birgit,Pietruszka, J?rg
, p. 7674 - 7681 (2018/11/02)
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).
rac-Altersolanol A and Related Tetrahydroanthraquinones, Total Synthesis and Cytotoxic Properties
Krohn, Karsten,Markus, Helga,Kraemer, Hans Peter,Frank, Walter
, p. 1033 - 1042 (2007/10/02)
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.