Stereoselective Synthesis of the Revised Structure of γ-Lactone Polyketide from Diaporthe sp. SXZ-19 and Its C-8 Epimer

Abstract

Revised structure of γ-lactone polyketide from Diaporthe sp. SXZ-19 and its C8-epimer were synthesized from TBS protected (S)-lactaldehyde and 2,3-O-cyclohexylidene-d-glyceraldehyde, which was derived from d-mannitol. The target γ-lactones were prepared via a common alkyne intermediate utilizing alkyne-aldehyde coupling reactions by changing the reaction conditions. In addition, Carreira and Ohira–Bestmann reactions were used as key steps to achieve the targets.

Key words

natural product - C8-epimer - d-mannitol - Carreira reaction - Ohira–Bestmann reaction

• References

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