Spiro[3.5]nonenyl Meroterpenoid Lactones, Cryptolaevilactones
G–L, an Ionone Derivative, and Total Synthesis of Cryptolaevilactone
M from Cryptocarya laevigata
Posted on 2019-08-23 - 15:05
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.
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Tsurumi, Fumika; Miura, Yuta; Nakano, Misaki; Saito, Yohei; Fukuyoshi, Shuichi; Miyake, Katsunori; et al. (2019). Spiro[3.5]nonenyl Meroterpenoid Lactones, Cryptolaevilactones
G–L, an Ionone Derivative, and Total Synthesis of Cryptolaevilactone
M from Cryptocarya laevigata. ACS Publications. Collection. https://doi.org/10.1021/acs.jnatprod.8b00732
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AUTHORS (10)
FT
Fumika Tsurumi
YM
Yuta Miura
MN
Misaki Nakano
YS
Yohei Saito
SF
Shuichi Fukuyoshi
KM
Katsunori Miyake
DN
David J. Newman
BO
Barry R. O’Keefe
KL
Kuo-Hsiung Lee
KN
Kyoko Nakagawa-Goto