1993
DOI: 10.1016/0040-4039(93)85077-a
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Asymmetric dihydroxylation of geranyl, neryl and trans, trans-farnesyl acetates

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Cited by 74 publications
(39 citation statements)
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“…Vidari et al [22] have described an efficient, highly enantioselective dihydroxylation of geranyl acetate (92% yield, 98% ee) employing the AD-mix system developed by Sharpless and co-workers. [23] In our case, however, treatment of 5 with AD-mix-a gave only a 10% yield of diol (À)-9 (Scheme 3), which still had to be transformed into epoxide 3.…”
Section: Resultsmentioning
confidence: 98%
“…Vidari et al [22] have described an efficient, highly enantioselective dihydroxylation of geranyl acetate (92% yield, 98% ee) employing the AD-mix system developed by Sharpless and co-workers. [23] In our case, however, treatment of 5 with AD-mix-a gave only a 10% yield of diol (À)-9 (Scheme 3), which still had to be transformed into epoxide 3.…”
Section: Resultsmentioning
confidence: 98%
“…13h Alternatively, catalytic asymmetric dihydroxylation of geranyl acetate in the presence of AD-mix-β at 0°C for 24 h gave (-)-6(S),7dihydroxy-geraneol, whereas AD-mix-α gave (+)-6(R),7-diol. [18,19] Similar treatment of farnesyl acetate through terminal double bond dihydroxylation, mesylation and base catalysed elimination yielded 10(S),11-epoxy-farnesyl acetate ( Table 1, entry 17). [18,19] Similar treatment of farnesyl acetate through terminal double bond dihydroxylation, mesylation and base catalysed elimination yielded 10(S),11-epoxy-farnesyl acetate ( Table 1, entry 17).…”
Section: Resultsmentioning
confidence: 99%
“…To this purpose we prepared (10S)-10,11-epoxy-farnesyl acetate (8) starting from (2E,6E)-farnesyl acetate (6) using a procedure described by Vidari et al 12 Highly enantioselective dihydroxylation of (2E,6E)-farnesyl acetate (6) employing AD-mix-b afforded diol 7. Conversion of diol 7 to the corresponding 10-O-mesylate followed by reaction with K 2 CO 3 in CH 3 OH gave (10S)-10,11-oxidofarnesol, which was subjected to acetylation affording 8.…”
Section: Resultsmentioning
confidence: 99%
“…The combined organic phases were dried (anhydrous Na 2 SO 4 ), filtered, and evaporated in vacuo. The crude product was flash chromatographed (from 15% AcOEt in petroleum ether to pure AcOEt) to afford 32 mg (58%) of 13 as white matt solid,12.6 mg (23%) of D 8,9 double bond isomer 14 as a white solid. Compound 13: [Found: C, 68.67; H, 11.35.…”
mentioning
confidence: 99%