Enantioselective Total Synthesis of (−)‐Blennolide A | Zendy

Tietze Lutz F. | Zendy; Ma Ling | Zendy; Reiner Johannes R. | Zendy; Jackenkroll Stefan | Zendy; Heidemann Sven | Zendy

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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

Abstract 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.

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