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Total Synthesis of (±)-2-Pupukeanone

✍ Scribed by Georg Fráter; Jean Wenger

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
338 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

(±)‐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.

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