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Asymmetric Synthesis of (+)‐Altholactone: A Styryllactone Isolated from Various Goniothalamus Species
Author(s) -
Enders Dieter,
Barbion Julien
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701647
Subject(s) - aldol reaction , moiety , chemistry , stereochemistry , stereoselectivity , enantioselective synthesis , alkylation , ring (chemistry) , total synthesis , tetrahydrofuran , diol , organic chemistry , catalysis , solvent
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 α‐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.