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A CH 3 OH-CH 2 Cl 2 (1:1) extract (N025439) of the leaves and twigs of Cryptocarya laevigata furnished eight new compounds, 1 - 8 . Based on extensive 1D and 2D NMR spectroscopic data examination, the new δ-lactone derivatives 1 - 6 are monoterpene-polyketide hybrids containing a unique spiro[3.5]nonenyl moiety. Their trivial names, cryptolaevilactones G-L, follow those of the related known meroterpenoids cryptolaevilactones A-F. Cryptolaevilactone L ( 6 ) contains 11,12- cis -oriented substituents, while the other cryptolaevilactones contain trans -oriented groups. The structure of the linear δ-lactone 7 , cryptolaevilactone M, was characterized from various spectroscopic data analysis, and the absolute configuration was determined by total synthesis through stereoselective allylation and Grubbs olefin metathesis. Compound 8 was elucidated to be an ionone derivative with a 3,4- syn -diol functionality.

journal of natural products

Spiro[3.5]nonenyl Meroterpenoid Lactones, Cryptolaevilactones G–L, an Ionone Derivative, and Total Synthesis of Cryptolaevilactone M from <i>Cryptocarya laevigata</i>

Spiro[3.5]nonenyl Meroterpenoid Lactones, Cryptolaevilactones G–L, an Ionone Derivative, and Total Synthesis of Cryptolaevilactone M from Cryptocarya laevigata