Asymmetric synthesis of (+)-altholactone: a styryllactone isolated from various Goniothalamus species |
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Authors: | Enders Dieter Barbion Julien |
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Affiliation: | Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany. Enders@RWTH-Aachen.de |
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Abstract: | 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 alpha-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 delta-lactone conversion and a stereoselective ring-closure to generate the annulated tetrahydrofuran moiety with inversion of configuration. |
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Keywords: | aldol reaction altholactone asymmetric synthesis hydrazones natural products |
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