total synthesis of arboridinine -...
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Total Synthesis of Arboridinine
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Features of Arboridinine
isolated in 2015
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Representative Alkaloids Sharing Similar Patterns with Arboridinine
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Retrosynthetic Analysis of Arboridinine
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Racemic and EnantioselectiveSyntheses of the Tricyclic Core
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Org. Lett. 2010, 12, 3104-3107
J. Am. Chem. Soc. 2011, 133, 1772–1774
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Screening of Conditions To Enantioselectively Acetylate Diol 17
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Completion Total Synthesis of Arboridinine
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Angew.Chem.Int.Ed.2015,54,9546–9549
Angew.Chem.Int.Ed.2016,55,13798–13802
Ag-Based 6-endo Dig Cyclization of 12
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Strategic Disconnection of Arboridinine
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Investigation of Double-Mannich Cyclization
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Construction of Bicyclic Indole Framework
Tetrahedron 2012, 68, 1017-1028
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Synthesis of Deoxyarboridinine
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Transformation of Ketone (Aldehyde) Into Alkene
Wittig reaction
Horner-Wadsworth-Emmons olefination (HWE olefination)
Tebbe olefination/ Petasis-Tebbe olefination
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Julia-Lythgoe olefination
Peterson olefination
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Takai-Utimoto olefination (Takai reaction)
Takai-Lombardo Reaction
Takeda Olefination Org. Lett. 2004, 6, 4961
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Nysted reagent
P: Wittig, HWETi: Tebbe, Petasis, Takai-Lombardo, Takeda, McMurryS: Julia Si: PetersonCr: Takai-UtimotoZn: Nysted
Bamford-Stevens-Shapiro reaction
McMurry coupling
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Revised Retrosynthetic Analysis
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Studies of Asymmetric Michael Addition
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Total Synthesis of (+)-Arboridinine
Org. Lett. 2015, 17, 4476-4478
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13-step racemic synthesis and 16-step formal asymmetric synthesis
14-step asymmetric total synthesis
Comparison between these Two Syntheses
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