1974
DOI: 10.1039/c3974000350b
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Biosynthesis of narcissidine

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Cited by 15 publications
(13 citation statements)
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“…These data also agree with the reported biosynthesis of haemanthamine (46a) in "King Alfred" daffodils (29,30), in "Texas" daffodils (28), in Sempre Avanti daffodils (32), and in Ismene hybrid "Sulphur Queen" (32). In all cases the biological conversion of either tyrosine (3) or 0-methylnorbelladine (^) into haemanthamine (46a) occurred with the loss of the pro-R hydrogen from C-2 ot ^ .…”
Section: Biosynthetic Investigations R Bifida Feeding Experimentssupporting
confidence: 82%
See 1 more Smart Citation
“…These data also agree with the reported biosynthesis of haemanthamine (46a) in "King Alfred" daffodils (29,30), in "Texas" daffodils (28), in Sempre Avanti daffodils (32), and in Ismene hybrid "Sulphur Queen" (32). In all cases the biological conversion of either tyrosine (3) or 0-methylnorbelladine (^) into haemanthamine (46a) occurred with the loss of the pro-R hydrogen from C-2 ot ^ .…”
Section: Biosynthetic Investigations R Bifida Feeding Experimentssupporting
confidence: 82%
“…This showed that 0-methylnorbelladine (^) was converted into haemanthamine (46a) with the loss of the pro-R hydrogen from C-2 of Also, the hydroxylation at C-11 occurred with retention of configuration ( Figure 18) . (4 7a) (32). These data showed that 0-methylnorbelladine (9) was converted into haemanthamine (46a) with loss of the pro-R hydrogen and that the hydroxylation at C-11 occurred with retention of configuration ( Figure 18).…”
Section: Late-stage Modificationsmentioning
confidence: 68%
“…Thus, as for cinnamaldehyde (E)-14, the addition to C ␤ -re face of a D − from the cofactor (which has exchanged the hydrogen to be delivered in the reduction with deuterated water [19]) and of a D + to C ␣ -re face from the solvent gave the deuterated saturated aldehyde shown in Scheme 5a, which was then reduced by one of the alcohol dehydrogenases active in fermenting BY to afford compound 21. The absolute configuration of the stereogenic centres C 2 and C 3 in compound 21 was thus assigned to be (2S,3S), while that of C 1 was established to be R on the basis of the known mode of BY reduction of the carbonyl group of cinnamaldehyde [20,21]. The sample contained also 23% of the diastereoisomer (1R,2R,3S)-21, due to the lower stereoselectivity of the bioreduction when the substrate was added in ethanol solution.…”
Section: Resultsmentioning
confidence: 99%
“…Deuterium labeling allowed insights into the course of the reaction [402,403]. This acyloin-type condensation reaction has been used quite successfully in the total synthesis of vitamin E [404,405], rare sugars [406], and several chiral synthons [251,398,402,.…”
Section: C─c Bond-forming and Breaking Reactionsmentioning
confidence: 99%