2009
DOI: 10.1021/jo9008645
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Biomimetic Total Synthesis of (±)-8-Oxoerymelanthine

Abstract: Erymelanthine 1 and 8-oxoerymelanthine 2 are unique erythrina alkaloids containing a pyridine ring. We synthesized (+/-)-8-oxoerymelanthine 2 in 2.0% overall yield using the following key reactions. The characteristic 6-5-6-6-membered ring system was constructed by the stereoselective intermolecular Diels-Alder reaction. Oxidative cleavage of the aromatic D-ring was conducted chemo- and regioselectively by ozonolysis in the presence of BF(3)-etherate. This cleavage site is identical to the site cleaved during … Show more

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Cited by 35 publications
(15 citation statements)
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“…The synthetic utility of the newly installed 2-sulfonate functional handle was next demonstrated through a series of product derivatizations to install H, aryl, heteroaryl, alkyl, and amino substituents (Scheme 3). For example, 22 can be reduced to give the 2,4-substituted pyridine 43 in 89 % yield, [20] and it also readily undergoes S N Ar with morpholine to give 44 in 85 % yield. [21,22] The pyridine substrates are compatible with traditional cross-coupling methodologies, thus leading to diverse 2,4,6-substituted pyridines.…”
mentioning
confidence: 99%
“…The synthetic utility of the newly installed 2-sulfonate functional handle was next demonstrated through a series of product derivatizations to install H, aryl, heteroaryl, alkyl, and amino substituents (Scheme 3). For example, 22 can be reduced to give the 2,4-substituted pyridine 43 in 89 % yield, [20] and it also readily undergoes S N Ar with morpholine to give 44 in 85 % yield. [21,22] The pyridine substrates are compatible with traditional cross-coupling methodologies, thus leading to diverse 2,4,6-substituted pyridines.…”
mentioning
confidence: 99%
“…For example, 22 can be reduced to give the 2,4-substituted pyridine 43 in 89 % yield, [20] and it also readily undergoes S N Ar with morpholine to give 44 in 85 % yield. [21,22] The pyridine substrates are compatible with traditional cross-coupling methodologies, thus leading to diverse 2,4,6-substituted pyridines.…”
Section: Methodsmentioning
confidence: 99%
“…Therefore, their structures with various biological properties have recently attracted attention as a synthetic target. 9,10) In previous papers, we described the isolation and structural characterization of an indole derivative, hypaphorine, and its sleep-inducing effect on normal mice, 11) as well as the isolation and structural characterization of a new Erythrinan alkaloid, erysodine N-oxide, together with known compounds, and the evaluation of the isolated compounds in terms of the enhanced activity for tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL). 12) In this paper, we describe the isolation and structural elucidation of four new Erythrinan alkaloids (1-4), including novel sulfated alkaloids from the high polarity portion extracted with n-BuOH, of the seeds of Erythrina velutina.…”
Section: )mentioning
confidence: 99%