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Total synthesis of Amphidinolide E:
Reference: Va, P.; Roush, W. R. J. Am. Chem. Soc. 2006, 128, 15960. DOI
Keywords: Alkyl-OH -> Aldehyde-α-OR • Mg-Vinyl+Aldehyde • Hydroboration Alkene • Alkyl-OH -> Aldehyde • Corey-Fuchs • Diol-1,2 cleavage • B-Allyl+Aldehyde • O-H -> O-SiEt3 • O-PMB -> O-H • Ketal -> Diol • Hydrostannation Alkyne • Pd/Sn-Vinyl+Vinyl-X • Stille coupling • RCM -> Lactone • Lactone-15+ • Claisen-Johnson • Fritsch-Buttenberg-Wiechell • Aldehyde -> Alkyne • Protecting group - Diene • Si-Alkyl -> H-Alkyl • Sn-Vinyl -> Vinyl-I • CarboxEster -> Aldehyde • Si-Allyl+Aldehyde • Ether-5 • O-H -> O-SiEt3 • Si-Alkyl -> H-Alkyl •
Reagents: DMSO, (COCl)2 • Vinyl-MgX • Orthoacetate • AlHiBu2 • 9-BBN-H • H2O2, NaOH • DMSO, Py·SO3 • PPh3=CBr2 • BuLi(n) • Acetic acid • Periodate, sodium • Allyl-B(tartrate) • HSiEt3 • BF3·OEt2 • Fluoride, Bu4N+ • HSiEt3 • 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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