An organic chemistry minilecture on the Enantioselective Total Synthesis of ( )-Aberrarone by Willi M. Amberg and Erick M. Carreira*. It features a remarkable cyclization cascade that forms four rings and six stereocentres in one step.
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References:
J. Am. Chem. Soc. 2022, 144, 26, 11574–11579 (This work)
. Chem. 2009, 74, 7581−7584 (Isolation)
Tetrahedron 2015, 71, 5918−5924 (studies towards the construction of the ring system)
J. Am. Chem. Soc. 2000, 122, 8, 1806–1807 (Alkyne addition)
J. Am. Chem. Soc., 2006,128, 1442–1443 (Meyer Schuster)
J. Am. Chem. Soc. 2005, 127, 48, 16804–16805 (Meyer Schuster)
Chem. Sci., 2019,10, 8219-8223 (Cyclization Cascade)
Org. Lett. 2007, 9, 11, 2207–2209 (Au Catalysed cyclopropanation)
Chem. Rev. 2021, 121, 14, 8613–8684 (Review on Au catalyzed synthesis of small rings)
J. Am. Chem. Soc. 1976, 98, 1, 300–301 (Riley oxidation mechanism)
0:00 Introduction
1:03 Strategy: Cyclization Cascade
1:38 Alkyne Addition
2:11 Deprotection
2:15 Acetylation
2:35 Alkylation
3:01 Xanthate Formation
3:17 Barton-McCombie Deoxygenation
3:50 Triflate Formation
4:16 Sonogashira Coupling
4:54 Parikh-Doering Oxidation
6:55 Reduction
7:06 Reductive Ring Opening
7:58 Riley Oxidation
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