np8b00732_si_001.pdf (4.79 MB)
Spiro[3.5]nonenyl Meroterpenoid Lactones, Cryptolaevilactones G–L, an Ionone Derivative, and Total Synthesis of Cryptolaevilactone M from Cryptocarya laevigata
journal contribution
posted on 2019-08-23, 15:05 authored by Fumika Tsurumi, Yuta Miura, Misaki Nakano, Yohei Saito, Shuichi Fukuyoshi, Katsunori Miyake, David J. Newman, Barry R. O’Keefe, Kuo-Hsiung Lee, Kyoko Nakagawa-GotoA CH3OH–CH2Cl2 (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.