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Total synthesis of Steenkrotin A:
Reference: Ding, H. et al Angew. Chem. Int. Ed. 2015, 54, 6905. DOI
Keywords: Ketone → EnolSilane • Ketone → EnolSilane • CarboxEster → Alkyl-OH • O-H → O-C(O)R • O-SiMe2tBu → O-H • O-H → O-Ethoxyethyl • O-H → O-C(O)R • Acetal → Hemiacetal • Alkyl-OH → Ketone • Alkyl-OH → Aldehyde • Rubottom oxidation • Ketone → Ketone-α-OR • Li-Allyl+Ketone • Ketone+Li-Alkyl • Carbene Cycloaddition • O-H → O-Alkyl • CarboxEster enolate+Alkyl-X • Alkyl-OH → Aldehyde • Prins • Radical cyclization(Alkyl) • Sm-Alkyl+Aldehyde • Aldehyde+Sm-R • Retro-Aldol • Aldol-K → Aldol • Aldol-K → Aldol • ConjAdd M-OR • Mechanism • Dehydroalkoxylation → Enone • Retro-Aldol • Ketone epimerization •
Reagents: SiMe2tBu-OTf • Perbenzoic acid, 3-chloro • CrO3Cl·PyH (PCC) • SiMe3-OTf • BuLi(n) • MeI • AlH4-Li+ • Acetic anhydride, NEt3 • Dess-Martin • HF·Py • SmI2 • HMPA (solvent) • Benzoyl peroxide • SmI2 • Dess-Martin • Carbonate, potassium • Hydroxide, lithium •

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