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Total synthesis of Dihydrocompactin (partial):
Reference: Burke, S. D., Saunders, J. O.; Oplinger, J. A.; Murtiashaw, C. W. Tetrahedron Lett., 1985, 26, 1131. DOI
Keywords: CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Jones oxidation • Aldehyde → CarboxAcid • CarboxAcid → CarboxCl • Claisen-Ireland • Claisen-Enol ether • Wittig-methoxymethyl • Reductive formylation • Cationic cyclization • Si-Vinyl+Carbenium • Li-SiR3+Aldehyde • Enal+Li-SiR3 • Jones oxidation • Mechanism •
Reagents: Crotonaldehyde • LiSiR3 • LiNiPr2 • SiMe2tBu-Cl • Diazomethane • AlH4-Li+ • CrO3·Py2 (Collins) • Vinyl-MgX • Vinyl-OR • Hg(OTFA)2 • PPh3=CH-OMe • CrO3, H2SO4 (Jones) • Oxalyl chloride • BH(sBu3)-K+ • P(O)Ph2CH2-R • AlHiBu2 • NaH • CrO3, H2SO4 (Jones) • SbCl5

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