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