1979
DOI: 10.1007/bf00987840
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An efficient synthesis of muscalure from jojoba oil or oleyl alcohol

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Cited by 16 publications
(6 citation statements)
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“…Finally, hydride reduction of 8 afforded a fluoro alcohol 9 (84%) which was converted to the corresponding mesylate 10 for glyceryl ether preparation (Baumann, 1972; Baumann and Mangold, 1964). Preparation of 10 was accompanied by the production of a compound identified as the -fluorohexadecenyl chloride 20, the production of which was associated with the use of prolonged reaction times and undistilled methanesulfonyl chloride (Shani, 1979).…”
Section: Resultsmentioning
confidence: 99%
“…Finally, hydride reduction of 8 afforded a fluoro alcohol 9 (84%) which was converted to the corresponding mesylate 10 for glyceryl ether preparation (Baumann, 1972; Baumann and Mangold, 1964). Preparation of 10 was accompanied by the production of a compound identified as the -fluorohexadecenyl chloride 20, the production of which was associated with the use of prolonged reaction times and undistilled methanesulfonyl chloride (Shani, 1979).…”
Section: Resultsmentioning
confidence: 99%
“…(1978), Rossi et a1. (1981), Shani (1979), Still and Mitra (1978), Uchida et a1. (1977) Farnum et al (1977), Pirkle and Rinaldi (1979) BierI- Leonhardt et al (1980, Mori et al (1978a,b), Uchida et al (1981) Hoshino and (a) Diethyl tartrate Rossiter et al (1981), Mori and Veda (1981) 9.…”
Section: Other Reactions Frequently Employed For Sex Pheromone Smentioning
confidence: 96%
“…(1981), Pirkle and Adams (1979), Tsuboi et a1. (1982) Mori ( Babler and Invergo (1979), Chuman et al (1979), Kocienski and Ansell (1977), Labovitz et al (1975), Mori and Kuwahara (1982), Pirkle and Boeder (1978), Pirkle and Adams (1979), Place et al (1978), Suguro et al (1981 Hammoud and , Place et al (1978), Still and Mitra (1978) Still (1979) Mori (1978) Suguro et al (1981) Bartlett et al (1982) Rossi and Marasco (1980) Tamada et al (1978) The following reactions were mediated by copper as cuprates RMgX, alkyl halide or tosylate Descoins et al (1977), Guss et al (1983), Mandai et al (1979), Mori et al (1978bMori et al ( , 1981a, Rossi (1978b), Shani (1979), Sonnet and Heath (1982a,b), Suguro and Mori (1979b) …”
mentioning
confidence: 95%
“…Infrared (IR) and nuclear magnetic resonance (NMR) spectra provided monitors for the chemical change occurring in each reaction. Purity was determined by NMR (16). All NMR spectra gave the following: terminal CH3 as triplet at 5 0.92-0.94; an intense signal at 1.2-1.4 for all aliphatic hydrogens; a signal at 1.98-2.05 for allylic hydrogens; and a quintet at 5.20 (J=5 cps) for the olefinic hydrogens.…”
Section: Generalmentioning
confidence: 99%
“…The mesylate (VI) was best prepared using (C2H5)3 N as a base. (When pyridine was used as a base, jojobyl pyridinium mesylate contaminated the product [16]). The iodide (VII) was readily prepared from the mesylate with NaI in acetone (see Scheme 3).…”
Section: R1-r 3 = Various Alkyl Groupsmentioning
confidence: 99%