Journal of the Chemical Society. Perkin transactions I p. 105 - 108 (1981)
Update date:2022-08-05
Topics:
Banthorpe, Derek V.
Christou, Paul N.
Artemiseole, an ether isolated from Artemisia tridentata, has been proved to be 1,4,4-trimethyl-6-vinyl-3-oxabicyclo<3.1.0>hexane by an unambiguous synthesis in six steps from 1-chloro-2-methylpropene, and is thus an irregular monoterpene of the santolinyl class.The availability of 3,6,6-trimethyl-5,6-dihydr-2H-pyran as an unexpected minor product of one of the steps allowed an efficient eight-step syntesis 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 had previously been prepared only by a fifteen-stage process.
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Doi:10.1021/ja00398a058
(1981)Doi:10.1021/jo00328a043
(1981)Doi:10.1016/0040-4039(81)80072-X
(1981)Doi:10.1039/P19810000887
(1981)Doi:10.1016/0223-5234(87)90289-3
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