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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.

ABSTRACT: A 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.

SUBMITTER: Tsurumi F 

PROVIDER: S-EPMC8495473 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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

Tsurumi Fumika F   Miura Yuta Y   Nakano Misaki M   Saito Yohei Y   Fukuyoshi Shuichi S   Miyake Katsunori K   Newman David J DJ   O'Keefe Barry R BR   Lee Kuo-Hsiung KH   Nakagawa-Goto Kyoko K  

Journal of natural products 20190823 9

A CH<sub>3</sub>OH-CH<sub>2</sub>Cl<sub>2</sub> (1:1) extract (N025439) of the leaves and twigs of <i>Cryptocarya laevigata</i> furnished eight new compounds, <b>1</b>-<b>8</b>. Based on extensive 1D and 2D NMR spectroscopic data examination, the new δ-lactone derivatives <b>1</b>-<b>6</b> 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. Cryptola  ...[more]

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