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Total Synthesis of (−)-Bipolarolide D 

Simplifying Synthesis
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An organic chemistry minilecture on the 'Concise Total Synthesis of (−)-Bipolarolide D' by Shengling Sun, Qi Wei, Yufei Liu, and Zhaohong Lu*. It features a highly effective [6+6] cycloaddition, a ring closing Heck Coupling and a Babler -Dauben Oxidation.
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References:
J. Am. Chem. Soc. 2024, 146, 21, 14427-14432 (This work)
Angew. Chem., Int. Ed. 2019, 58, 12091−12095 (Isolation)
Organic Reactions, 1-221. (PDC Oxidation)
J. Am. Chem. Soc. 2011, 133, 20175−20185 ([6+2] cycloaddition)
J. Org. Chem. 1991, 56, 4093−4094 (Heck)
Tetrahedron 1993, 49, 1773−1782 (Heck)
J. Am. Chem. Soc. 2017, 139, 10, 3643-3646 (Rh Isomerization)
Chem. Rev. 2003, 103, 1, 27-52 (Allylic Oxidation)
J. Am. Chem. Soc. 1950, 72, 1, 218-219 (Butenyl Grignard Addition)

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6 сен 2024

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Комментарии : 8   
@UniCorneliusfan21
@UniCorneliusfan21 Месяц назад
It’s a good day when simplifying synthesis uploads Also I think the thionyl chloride elimination should proceed via the hemiacetal oxygen attacking thionyl chloride instead of the open chain form alcohol
@dzhangarbadmaev1057
@dzhangarbadmaev1057 Месяц назад
Thank you for taking the time to make such instructional videos!
@aidanlooby
@aidanlooby Месяц назад
It has been a few months now and I am still not over this synthesis! The fulvene chemistry is absolutely crazy and using a Heck reaction to essentially close the tetracyclic core is amazing. Love the channel!
@KrashFries
@KrashFries Месяц назад
2:48 the chromate ester elimination produces a Cr(IV) species, which should have the nominal formula H2CrO3. note that Cr(IV) is unstable and tends to decay to Cr(III) and eventually solid Cr2O3 (ask the solid state chemists or nanochemists about that mechanism, i’m out).
@Reaboian
@Reaboian Месяц назад
Oh the one synthesis workshop did a podcast on, this is a really typical and cute molecule
@Chemicator
@Chemicator Месяц назад
What a fascinating structure! Perfect explanation.👍🧪
@samjo475
@samjo475 Месяц назад
at 8:08 I think is should be PPh3 and not Ph3
@SimplifyingSynthesis
@SimplifyingSynthesis Месяц назад
Yep that's a typo. Good catch!
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