1032514-41-2Relevant academic research and scientific papers
Asymmetric synthesis of (+)-altholactone: A styryllactone isolated from various goniothalamus species
Enders, Dieter,Barbion, Julien
experimental part, p. 2842 - 2849 (2009/04/07)
The asymmetric total synthesis of (+)-altholactone (1), a member of the styryllactone family of natural products displaying cytotoxic and antitumor activities, is described. Key steps include a RAMP-hydrazone a-alkylation (RAMP = (R)-1-amino-2-methoxymethylpyrrolidine) of 2,2-dimethyl-1,3-dioxan-5-one, a boron-mediated aldol reaction, a six- to five-membered ring acetonide shuffling, an oxidative 1,5-diol to δ-lactone conversion and a stereoselective ring-closure to generate the annulated tetrahydrofuran moiety with inversion of configuration.
