Premium
Enantioselective Total Synthesis of (−)‐Diversonol
Author(s) -
Tietze Lutz F.,
Jackenkroll Stefan,
Raith Christian,
Spiegl Dirk A.,
Reiner Johannes R.,
Ochoa Campos Maria Claudia
Publication year - 2013
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.201204037
Subject(s) - enantioselective synthesis , dihydroxylation , chemistry , intramolecular force , wittig reaction , carbonylation , total synthesis , sharpless asymmetric dihydroxylation , moiety , domino , acylation , yield (engineering) , diastereomer , stereochemistry , organic chemistry , catalysis , carbon monoxide , metallurgy , materials science
For the synthesis of (−)‐diversonol ( ent ‐ 1 ), an enantioselective domino‐Wacker/carbonylation/methoxylation reaction and an enantioselective Wacker oxidation were used to give the chroman in high yield and 96 % and 93 % ee , respectively. Dihydroxylation at the vinyl moiety using the Sharpless procedure and a Wittig–Horner reaction followed by hydrogenation, benzylic oxidation, and an intramolecular acylation provided the tetrahydroxanthenone, from which ent ‐ 1 is accessible in a few steps. Furthermore, the synthesis of the diastereomeric diversonol rac ‐1,9 a‐ epi ‐diversonol ( rac ‐ 41 ) is also described.