Total Synthesis of Cinnamodial-Based Dimer (–)-Capsicodendrin

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An organic chemistry lecture on the Total Synthesis of Cinnamodial-Based Dimer (–)-Capsicodendrin by Youngho Jang and Sunkyu Han*

Erratum:
The stereoselectivity of the epoxidation is driven by steric hindrance from the axial methyl group, not the TBS group which I say at 7:50

References:
J. Org. Chem. 2020, 85, 11, 7576–7582 (This work)
Chem. Lett. 1980,9, 445-446 (Oishi Synthesis)
J. Am. Chem. Soc. 1981, 103, 11, 3226–3228 (White Synthesis)

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DBU mediated elim to generate the ketone at 8:12 is most likely E1CB. Approach by DBU at the alpha face for anti-elim is hindered by the vicinal silyl carbinol.

singularityJoe
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great vídeo m8! One thing ended up coming to mind, how did the stereochemistry of the OAc bond inverted at 11:15?

matheussales
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Great video! There was one thing that I did not follow though. You mention that the stereoselectivity of the epoxidation is driven by the bulky TBS groups. But how could that be since they are bonded the the alkene and thus should be 'flat" ?

Marnixvdkolk
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