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J. -L. Capman, and W. Chodkiewicz, Bull. Soc. chim. France, 1971, 2248. C. Metge and C. Bertrand, Compt. , 1971, 272, C, 318. 5809. 106 107 Monoterpenoids 29 synthesis (Scheme 4) of 2-methyl-trans-menth-2-ene (148a ; R = H), required for the synthesis of the sesquiterpene cubebene (see Chapter 2, p. 76). The yield of the two aldehydes (149)was always below 40 %, and it was not possible to convert the accompanying thio-diene (150) into the aldehyde (149). After reduction, the alcohols (148; R = OH) were separated as their trimethylsilyl ethers (148; R = OSiMe,), then converted into the hydrocarbons (148; R = H) via the bromides (148; R = Br).

Marshall, Tetrahedron Letters, 1971, 753. Monoterpenoids 41 the racemate, the cyclopentanonecarboxylic acid (212) was homologated by the Arndt-Eistert procedure, but for preparation of the optically active ( + )-fenchone, the cyclopentanone (211)was synthesized from a bromo-isofenchol(213) obtained from the reaction of (+)-a-pinene epoxide (214) or (-)-trans-pinocarveol (215) with hydrogen bromide. Treatment of the chloride (211)with ethoxide ion gave (+)-fenchone (210). 160 The ‘traditional’ way of making bicyclo[2,2,l]heptanes via a DielsAlder reaction was used in a synthesis of teresantalol (216).

Treatment of the chloride (211)with ethoxide ion gave (+)-fenchone (210). 160 The ‘traditional’ way of making bicyclo[2,2,l]heptanes via a DielsAlder reaction was used in a synthesis of teresantalol (216). A departure from the usual routine was the use of the allene (217) as dienophile. The required endo-acid (218)’ separated from the products by iodolactone formation and regeneration with zinc, was treated with 97% formic acid to give the tricyclene lactone (219). 16’ The exo-acid li Reagents: i, H C 0 , H ; ii, PhSNa; iii, esterify; iv, LiAIH,; v, Ni-H,; vi, Br,-CH,Cl, sodium salt.

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