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

Year: 2019
Type: article
Abstract: 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.
DOI: 10.1021/acs.jnatprod.8b00732
Authors: Fumika Tsurumi, Yuta Miura, Misaki Nakano, Yohei Saito, Shuichi Fukuyoshi, Katsunori Miyake, David J. Newman, Barry R. O’Keefe, Kuo-Hsiung Lee, Kyoko Nakagawa-Goto
Institutions: Kanazawa University, Tokyo University of Pharmacy and Life Sciences, National Institutes of Health, Frederick National Laboratory for Cancer Research, National Cancer Institute, Center for Cancer Research, University of North Carolina at Chapel Hill, China Medical University, China Medical University Hospital
Language: English
Open Access status: green
Awards: G1534035308, Discovery of antitumor drug candidates from rainforest plants, Novel Antitumor Agents, G386607036, Development of novel drug leads based on rare tropical resources, G5888954722, G9000186730
OpenAlex ID: W2969720419
FWCI: 0.573
Cites: 35
Cited by: 17
Related to: 10