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Syntheses of 2 naturally occurring mono terpenes with the santolinyl skeleton

Syntheses of 2 naturally occurring mono terpenes with the santolinyl skeleton

Journal of the Chemical Society Perkin Transactions I (1): 105-108

Artemiseole, an ether isolated from Artemisia tridentata, was proved to be 1,4,4-trimethyl-6-vinyl-3-oxabicyclo[3.1.0]hexane by an unambiguous synthesis in 6 steps from 1-chloro-2-methylpropene and is an irregular monoterpene of the santolinyl class. The availability of 3,6,6-trimethyl-5,6-dihyro-2H-pyran as an unexpected minor product of 1 of the steps allowed an efficient 8-step synthesis from the chloro-compound of (Z)-5-ethylidene-5,6-dihydro-3,6,6-trimethylpyran-2-one to be carried out: this is an irregular monoterpene lactone from Chrysanthemum flosculosum that was previously prepared only by a 15-stage process.

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