171523-63-0Relevant articles and documents
Total synthesis and stereochemical revision of (+)-aeruginosin 298-A.
Wipf,Methot
, p. 4213 - 4216 (2000)
[structure:see text] Novel routes toward both enantiomers of the bicyclic proline surrogate 2-carboxy-6-hydroxyoctahydroindole, i.e., Choi, were developed on the basis of the oxidative cyclization of L-tyrosine. Synthesis of the proposed sequence of (+)-a
Influence of base and structure in the reversible covalent conjugate addition of thiol to polycyclic enone scaffolds
Rosenker, Christopher J.,Krenske, Elizabeth H.,Houk,Wipf, Peter
supporting information, p. 1076 - 1079 (2013/04/10)
The energetics of thiol addition and elimination reactions to bicyclic enones derived from an indole core structure were explored using 1H NMR and density functional theory (DFT) calculations. The agreement between experiment and theory is exce
Asymmetric total syntheses of tuberostemonine, didehydrotuberostemonine, and 13-epituberostemonine
Wipf, Peter,Spencer, Stacey R.
, p. 225 - 235 (2007/10/03)
Detailed experimental approaches toward the pentacyclic Stemona alkaloids tuberostemonine and didehydrotuberostemonine and the close analogue 13-epituberostemonine are described. The syntheses originate with a hydroindolinone derivative that can be obtain
Stereodivergent routes from tyrosine to the 7-(R) and 7-(S) diastereomers of the 7-hydroxy-2,3,7,7a-tetrahydroindole ring found in gliotoxin
Henninger, Todd C.,Sabat, Michal,Sundberg, Richard J.
, p. 14403 - 14418 (2007/10/03)
Two routes from the oxidative cyclization product 1 derived from tyrosine to methyl 7-(tert-butyldimethylsiloxy)-N-(benzyloxycarbonyl)-2,3,7,7a-tetrahydro indole-2-carboxylate are described. The routes are stereodivergent leading to the 2-S,7-S,7a-S (6) and 2-S,7-R,7a-S-(13) diastereomers. The former stereochemistry corresponds to that present in gliotoxin.
Asymmetric total synthesis of the Stemona alkaloid (-)-stenine
Wipf, Peter,Kim, Yuntae,Goldstein, David M.
, p. 11106 - 11112 (2007/10/03)
Stenine can be extracted from the roots of the Chinese medicinal plant Stemona tuberosa (Stemonaceae), and its structure and absolute configuration were derived by comparison to the major Stemona alkaloid tuberostemonine. We report the first enantioselect