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Total synthesis of Amphidinolide E:
Reference: Va, P.; Roush, W. R. J. Am. Chem. Soc. 2006, 128, 15960. DOI
Keywords: Mg-Vinyl+Aldehyde • O-H → O-SiEt3 • Ketal → Diol-1,2 • Hydrostannation Alkyne • Pd/Sn-Vinyl+Vinyl-X • RCM → Lactone • Lactone-9+ • Claisen-Johnson • Fritsch-Buttenberg-Wiechell • Aldehyde → Alkyne • Protecting group - Diene • Sn-Vinyl → I-Vinyl • CarboxEster → Aldehyde • Si-Allyl+Aldehyde • Aldehyde+Si-R • Ether-5 • O-H → O-SiEt3 • Si-Alkyl → H-Alkyl • Mg-Vinyl+Aldehyde • Alkyl-OH → Aldehyde-α-OR • Hydroboration alkene • Alkyl-OH → Aldehyde • Corey-Fuchs • Ketal → Diol-1,2 • B-Allyl+Aldehyde • O-PMB → O-H • Diol-1,2 cleavage •
Reagents: DMSO, (COCl)2 (Swern) • Vinyl-MgX • Orthoacetate • AlHiBu2 • BH-BBN • H2O2, NaOH • DMSO, Py·SO3 (Parikh-Doering) • PPh3=CBr2 • BuLi(n) • Acetic acid • Periodate, sodium • Vinyl-SiR3 • Allyl-B(tartrate) • Chiral auxiliary-Boronate • SiEt3-Cl • BF3·OEt2 • Fluoride, R4N+ • SiEt3-OTf • DDQ • Benzoyl chloride, 2,4,6-trichloro • Ceric ammonium nitrate • Grubbs I • SnBu3-AlEt2 • CuCN • NIS • Acetic acid • Vinyl-SnR3 • Pd(PPh3)4 • CuCl • Imidazole • DMF (solvent) •

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