1987
DOI: 10.1039/p19870002377
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Enantiospecific synthesis of (+)-retronecine, (+)-crotonecine, and related alkaloids

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Cited by 46 publications
(20 citation statements)
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References 13 publications
(17 reference statements)
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“…All physical and spectral data were in good agreement with the literature. 25 rac-7,7-Dimethyl-2,6-dioxabicyclo[3.3.0]octane-3-one ((±)-8). The title compound was prepared according to general method 1 from diol (±)-7 (247 mg, 1.90 mmol).…”
Section: General Informationmentioning
confidence: 99%
“…All physical and spectral data were in good agreement with the literature. 25 rac-7,7-Dimethyl-2,6-dioxabicyclo[3.3.0]octane-3-one ((±)-8). The title compound was prepared according to general method 1 from diol (±)-7 (247 mg, 1.90 mmol).…”
Section: General Informationmentioning
confidence: 99%
“…Since the late 1970s, heterocyclic enamines have been investigated by Kishi, 2 Danishefsky, 3-5 Rapoport 6 and others in the synthesis of saxitoxin, camptothecin, mitomycins and alkaloids. [7][8][9][10][11][12] And recently, exo-cyclic enaminoesters have been employed in the the synthesis of carbacephems 13 , a new class of β-lactam antibiotics. One of the most noticeable features of heterocyclic secondary enamines 1 is their ambident bisnucleophilicity; nucleophilic reaction can occur at the enaminic carbon and/or the secondary amino nitrogen.…”
Section: Introductionmentioning
confidence: 99%
“…Buchanan et al reported that a silyl ether proved to be more tractable as a substrate for Dieckmann cyclisation. 31 Therefore, the alcohol was converted to its silyl ether using the procedure reported by Corey and Venkateswarlu. 32 The silyl ether (1.30) was obtained in good yield by treatment with tert-butyldimethylsilyl chloride and imidazole in dimethylformamide at 0 °C to room temperature for 24 hours (Scheme 1.11).…”
Section: Scheme 111mentioning
confidence: 99%
“…The relative configuration of the pyrrolidine (1.30) was assumed based on the cis- In the case of intramolecular condensation of bicyclic di-ester (1.36) by a Dieckmann reaction, this method has been reported to be useful for the synthesis of pyrrolizidine alkaloids. 31,[33][34][35] Geissman and Waiss 35 reported the Dieckmann condensation of lactone (1.36) was a direct consequence of the presence of the lactone ring (Scheme 1.13). They proposed that a carbonyl group at position 3 and a 7-hydroxyl group of the pyrrolizidine (1.37) would involve substantial strain.…”
Section: Scheme 111mentioning
confidence: 99%
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