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Total Synthesis of (±)‐2‐Pupukeanone
Author(s) -
Fráter Georg,
Wenger Jean
Publication year - 1984
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.19840670706
Subject(s) - chemistry , hydride , alcohol , lactone , sodium hydride , total synthesis , sodium , organic chemistry , medicinal chemistry , hydrogen
(±)‐2‐Pupukenone ( 4 ) has been synthesized, the key step being the intramolcular Diels‐Alder reaction of the intermediate 13 to 14 (42%) and 15 (14%). The bromodiene 12 has been obtained from the reaction of α‐isopropylidene‐γ‐lactone ( Scheme 2 ) 12 with sodium phenylselenide and subsequent esterification to 9 , oxidation and thermal elimination of which furnished 10 . Reduction of 10 with diisobutylaluminimum hydride and treatment of the resulting alcohol 11 with PBr 3 led to the required bromodiene 12 . Finally, hydrogenation of the 14 on Pt(C) in CH 3 OH gave a 4:1 mixture of 2‐pupukeanone ( 4 ) and epi‐2‐pupukeanone 16 .