1960
DOI: 10.1007/bf02170251
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The constitution of limonin

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1961
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Cited by 129 publications
(38 citation statements)
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“…In our experience as well (5)(6)(7), the addition of a carbalkoxy substituent can produce a substantial increase in reactivity relative to the unsubstituted parent system. Our interest in lactonic dienophiles stems from a projected synthesis of the citrus bitter principal limonin (1) (8,9). Carbethoxy activated lactone 2 would be a useful synthon for the introduction of the A' ring.…”
mentioning
confidence: 99%
“…In our experience as well (5)(6)(7), the addition of a carbalkoxy substituent can produce a substantial increase in reactivity relative to the unsubstituted parent system. Our interest in lactonic dienophiles stems from a projected synthesis of the citrus bitter principal limonin (1) (8,9). Carbethoxy activated lactone 2 would be a useful synthon for the introduction of the A' ring.…”
mentioning
confidence: 99%
“…This was the position in September, 1959, when Professor Robertson was able to state from the X-ray evidence (see Arigoni et at. 9 ) that limonin was either (VIII) or (XXXVIII). The latter formula is, of course, incompatible with much chemical evidence, and therefore formula (VIII) stands.…”
mentioning
confidence: 96%
“…Limonilic acid, C26H300916, was first obtained 18 by oxidation of limonin in alkaline solution with potassium permanganate, but it is more readily prepared in essentially quantitative yield by treatment of an alkaline solution of limonin with hypoiodite-", Limonilic acid is to be formulated as (XXXV) 9 making an ethereal linkage, facilitated, no doubt, by a specially favourable conformational situation,…”
mentioning
confidence: 99%
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“…Trijugin-type tetranor-triterpenoids (limo- nonids) like sandrapins are considered to be biogenetically produced via a pinacol-pinacolone rearrangement of methyl 9,11-dihydroxyangolensate (ekebergin-type limonoid), 11) which has the same configurations at C-5, C-10, C-13 and C-17 as those of limonin. 14) Taking account of these biogenetic considerations, sandrapins A-E are also presumed to have the absolute structures as shown in the formulas.…”
mentioning
confidence: 99%