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Synthesis of (±)‐Pyrenolide B
Author(s) -
Moricz Attila,
Gassmann Elisabeth,
Bienz Stefan,
Hesse Manfred
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780313
Subject(s) - chemistry , stereochemistry , combinatorial chemistry
Abstract In the synthesis of the title compound 12 , the important intermediate 7 was obtained in good yield from the easily available ethyl 5, 5‐ethylenedioxy‐2‐oxocyclohexane‐1‐carboxylate ( 1 ) via ring enlargement of the bicyclic enol ether 5 ( Scheme ). Its reduction (NaBH 4 in EtOH) and subsequent protection with ( t ‐Bu)Me 2 Si resulted in the highly functionalized ten‐membered lactone 9 . Introduction of the ( Z )‐configurated double bond, followed by deprotection and elimination of H 2 O, gave (±)‐pyrenolide B ( 12 ) in 16% overall yield.