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- W2080871298 abstract "Starting from the cheap isophorone derivative 1 and the alkynols 2–4, we could prepare the key intermediates 9–11 via addition reaction (→ 5–7) and hydrogenation. Ring closure of 9–11 led to the theaspirone (C) and/or ketoedulan (E) series, depending on the reaction conditions used and the steric situation at C-2. By treatment of 9 with tosyl chloride/pyridine the theaspirone derivative 13 was formed exclusively, whereas 10a, b were converted into mixtures of 14a, b together with the ketoedulan derivatives 20a, b; the crowded 11 did not react at all. By treatment of 9–11 with hydrochloric acid/acetone 19–21 were readily obtained. Several hydrogenation and dehydration steps under various conditions led to the theaspirones 16–18, to the ketoedulans 26a, b and 27, and to the edulans 39a and 40b. – Olfactory evaluation of the theaspirones 16 (harsh, green), 17a (floral, fruity) and 18 (weak, woody) shows the drastic influence of the steric situation at C-2. The ketoedulans 26a and 27 smell weak, woody. Evaluation of both odor and flavor of 39a and 40b exhibits mostly woody, camphoraceous and fruity tonalities." @default.
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- W2080871298 date "1994-04-12" @default.
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- W2080871298 title "Structure-Odor Correlation, XIX. Synthesis and Olfactory Properties of Various Racemic Theaspirones, Ketoedulans and Edulans" @default.
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