Chapter XI Alkaloids of the Amaryllidaceae

Cook, J. W.; Loudon, J. D.

doi:10.1016/s1876-0813(08)60028-7

Cited by 25 publications

(62 citation statements)

References 29 publications

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“…To a solution containing 4.0 g (9.9 mmol) of N-benzyl-N-furan-2-yl-2-iodo-benzamide 47 and 5.2 g (14 mmol) of methyl 2-tri-n-butyl stannylacrylate 28 in 40 mL of DMF under argon atmosphere was added 1.2 g (0.99 mmol) of Pd(PPh 3 ) 4 and 0.57 g (3.0 mmol) of Cul. The reaction mixture was stirred at rt for 20 min, followed by the addition of 2.3 g (15 mmol) of CsF.…”

Section: -Benzyl-24a-epoxy-6-oxo-24a56-tetrahydro-1h-phenanthridmentioning

confidence: 99%

“…After stirring for 1 h, the reaction mixture was allowed to warm to rt and was stirred until the color of the reaction mixture turned into green (ca 20 min). The reaction mixture was quenched with a saturated NH 4 Cl solution and extracted with CHCl 3 . The combined organic extracts were dried over MgSO 4 -7-benzyl-16,16-dimethyl-6-oxo-7,8,11,12,13,14-hexahydro-6H-15,17-dioxa-7-azacyclopenta[a]phenanthrene-9-carboxylic Acid Methyl Ester (28)…”

Section: -Benzyl-24a-epoxy-6-oxo-24a56-tetrahydro-1h-phenanthridmentioning

confidence: 99%

“…The mixture was stirred at room temperature for 12 h, quenched with a saturated NaHCO 3 solution, and extracted with EtOAc. The organic extracts were washed with H 2 O, brine and dried over MgSO 4 …”

Section: -Benzylmentioning

confidence: 99%

“…Upon cooling, 0.12 g (0.10 mmol) of Pd(PPh 3 ) 4 , and 0.5 g (0.5 mmol) of CuCl were added and the mixture was degassed 3 times under vacuum using an argon purge. To this mixture was added 8.4 mL of anhydrous DMSO, 0.5 g (1.0 mmol) of iodide 11, and 0.47 g (1.3 mmol) of methyl 2-tri-n-butyl stannylacrylate.…”

Section: -(4-methoxy-benzyl)-24a-epoxy-6-oxo-24a56-tetrahydro-1hmentioning

confidence: 99%

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Synthesis of Some Members of the Hydroxylated Phenanthridone Subclass of the Amaryllidaceae Alkaloid Family

Padwa

Zhang

2007

J. Org. Chem.

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The total synthesis of several members of the hydroxylated phenanthridone sub-class of the Amaryllidaceae alkaloid family has been carried out. (±)-Lycoricidine and (±)-7-deoxypancratistatin were assembled through a one-pot Stille/intramolecular Diels-Alder cycloaddition cascade to construct the core skeleton. The initially formed [4+2]-cycloadduct undergoes nitrogen-assisted ring opening followed by a deprotonation/reprotonation of the resulting zwitterion to give a rearranged hexahydroindolinone on further heating at 160 °C. The stereochemical outcome of the IMDAF cycloaddition has the side arm of the tethered vinyl group oriented exo with respect to the oxygen bridge. The resulting cycloadduct was used for the stereocontrolled installation of the remaining functionality present in the C-ring of the target molecules. Key features of the synthetic strategy include (1) a lithium-hydroxide induced tandem hydrolysis/decarboxylation/elimination sequence to introduce the required π-bond in the C-ring of (±)-lycoricidine; and (2) conversion of the initially formed Diels-Alder adduct into an aldehyde intermediate which then undergoes a stereospecific decarbonylation reaction mediated by Wilkinson's catalyst to set the trans B-C ring junction of (±)-7-deoxypancratistatin.The Amaryllidaceae alkaloids constitute an important class of naturally-occurring compounds.

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Section: -Benzyl-24a-epoxy-6-oxo-24a56-tetrahydro-1h-phenanthridmentioning

confidence: 99%

Section: -Benzyl-24a-epoxy-6-oxo-24a56-tetrahydro-1h-phenanthridmentioning

confidence: 99%

Section: -Benzylmentioning

confidence: 99%

Section: -(4-methoxy-benzyl)-24a-epoxy-6-oxo-24a56-tetrahydro-1hmentioning

confidence: 99%

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