Unified Total Syntheses of Benzenoid Cephalotane Norditerpenoids
An organic chemistry minilecture on the Unified Total Syntheses of Benzenoid Cephalotane-Type Norditerpenoids: Cephanolides and Ceforalides by Goh Sennari, Kristen E. Gardner, Stefan Wiesler, Maximilian Haider, Alina Eggert and Richmond Sarpong*. It features a lot of interesting reactions such as a thianthrenation, a Ru-catalysed photo oxidation and an Ir-catalysed protodeborylation.
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References:
J. Am. Chem. Soc. 2022, 144, 31, 14042–14046 (This work)
Phytochemistry 2021, 192, No. 112939 (Review of cephalotane diterpenoids)
J. Org. Chem. 1994, 59, 20, 6095–6097 Flouride accelerated Suzuki coupling)
Chem. Eur. J. 2013,19, 10082 – 10093 (Flouride accelerated Suzuki coupling)
Tetrahedron Lett. 1984, 25, 1953−1956. (Suarez oxidation)
Nature 2019, 567, 223−228. (Ritter thianthrenylation)
Chem. Sci. 2019, 10, 6210−6214 (Protodeborylation)
J. Org. Chem. 2001, 66, 23, 7741–7744 (Indium promoted deoxygenation)
Nature 2013, 499, 192−196. (PPO Oxidation)
Org. Lett. 2015, 17, 19, 4866–4869 (Pd- catalyzed carbonylation)
(J. Org. Chem. 2020, 85, 20, 12901–12911 (Thiourea-mediated bromination)
Chem. Sci., 2017,8, 7180-7185 (Photo oxidation)
Org. Biomol. Chem., 2018,16, 2324-2329 (Iodine-mediated dearomatization)
0:00 Introduction
0:16 Unified Total Syntheses of Benzenoid Cephalotane-Type Norditerpenoids: Cephanolides and Ceforalides
1:10 Strategy
1:55 Suzuki-Miyaura Coupling
2:25 Diels-Alder Cycloaddition
3:00 Methyl-Borylation/ Oxidation
3:34 DMP Oxidation
3:53 Reduction
4:04 Suarez Oxidation
4:50 Barton-McCombie Deoxygenation
5:44 Thianthrenation
6:44 Protodeboronation
7:19 Deprotection
8:28 Benzylic Oxidation
8:49 Methoxycarbonylation
9:55 Jones Oxidation
10:31 Bromination
11:14 Dehalogenation
11:48 Photo-Oxidation
12:32 Oxidative Cyclization
13:39 Oxidative Dearomatization