Efficient Asymmetric Syntheses of (+)-Strictifolione

Abstract

The asymmetric synthesis and a formal asymmetric synthesis of (+)-strictifolione are described. As key step in both approaches the Julia-Kocienski olefination to create an E-configured alkene was used. The anti-1,3-diol moiety was synthesized by employing a SAMP-hydrazone α,α′-bisalkylation/deoxygenation protocol and the stereocentre of the lactone unit is based on an enzymatic reduction with baker’s yeast. Alternatively, a lactone precursor could be efficiently synthesized by a (S)-proline catalyzed α-oxyamination of pent-4-enal.

Key words

asymmetric synthesis - enzymatic reduction - hydrazones - natural products - organocatalysis

References

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