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Enantioselective Total Synthesis of (−)‐Blennolide A
Author(s) -
Tietze Lutz F.,
Ma Ling,
Reiner Johannes R.,
Jackenkroll Stefan,
Heidemann Sven
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.201300479
Subject(s) - enantioselective synthesis , intramolecular force , domino , acylation , carbonylation , wacker process , chemistry , stereochemistry , total synthesis , organic chemistry , catalysis , palladium , carbon monoxide
Blennolide A can be synthesized through an enantioselective domino‐Wacker/carbonylation/methoxylation reaction of 7 a with 96 % ee and an enantioselective Wacker oxidation of 7 b with 89 % ee . Further transformations led to the α,β‐unsaturated ester ( E )‐ 17 , which was subjected to a highly selective Michael addition, introducing a methyl group to give 18 a . After a threefold oxidation and an intramolecular acylation, the tetrahydroxanthenone 4 was obtained, which could be transformed into (−)‐blennolide A ( ent‐ 1 ) in a few steps.