126178-08-3Relevant articles and documents
Asymmetric synthesis of synargentolide A and its 3-epimer using the RAMP-hydrazone methodology
Enders, Dieter,Reichenbach, Linus F.
, p. 959 - 965 (2013)
Synargentolide A was synthesized in 11 steps starting from the commercially available 2,2-dimethyl-1,3-dioxan-5-one, employing the SAMP/RAMP-methodology via an α,α′-bis-alkylation to generate the first two stereogenic centers with virtually complete asymmetric induction (de, ee >99%). After the asymmetric synthesis of the triol fragment of the molecule, the δ-lactone moiety was constructed using an asymmetric allylation, esterification, and ring-closing metathesis sequence. Georg Thieme Verlag Stuttgart - New York.
Stereoselective synthesis of advanced intermediates en route to Taxuspine U and X: a study of macrocyclization via ring closing metathesis to highly constrained twelve-membered rings
Galletti, Elena,Avramova, Stanislava I.,Renzulli, Michela L.,Corelli, Federico,Botta, Maurizio
, p. 751 - 754 (2007/10/03)
The stereoselective synthesis of an advanced intermediate of Taxuspine U and X has been accomplished using a ring closing metathesis strategy. The feasibility of ring closing metathesis in synthesizing highly constrained and functionalized macrocycles has been demonstrated provided the appropriate substrate structure and substitution pattern are chosen.
Asymmetric synthesis of protected 2-keto-1,3-diol and 1,2,3-triol building blocks bearing a quaternary stereogenic center
Enders,Nühring,Runsink,Raabe
, p. 1406 - 1414 (2007/10/03)
The asymmetric synthesis of protected 2-keto-1,3-diols 5 and 1,2,3-triols 6 bearing a quaternary stereogenic center starting from 2,2-dimethyl-1,3-dioxan-5-one (1) is described. The stereogenic centers are generated by sequential α-alkylation of 1 using the SAMP/RAMP hydrazone method and stereoselective reduction of ketones 5 with L-selectride. The products are obtained in good yields and high diastereomeric and enantiomeric excesses.