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Total synthesis of Leucascandrolide A:
Reference: Williams, D. R.; Patnaik, S.; Plummer, S. V. Org. Lett. 2003, 5, 5035. DOI
Keywords: O-PMB → O-H • Cu-Vinyl+EnoateAmide(Evans) • EnoateAmide(Evans)+Cu-R • ConjAdd Cu-R(asym) • Yamaguchi lactonization • Lactone-9+ • Sn-Rl → B-R • Li-Dithiane+Alkyl-X • Alkyl-X+Li-R • Alkyl-OH → Alkyl-I • Mukaiyama Aldol • Aldol-Si • Ether-6 • B-Allyl-Corey+Aldehyde • CarboxAmide(Evans) → Alkyl-OH • Si-Allyl → Br-Allyl • Allyl-X → Allyl-Sn • Alkene → Diol-1,2 • Alkene cleavage • Ketone → Alkyl-OH(asym) • Acetal → Aldehyde • Acetal(thio) → Acetal • O-H → O-Me • Enone → Allyl-OH(asym) • O-H → O-C(O)R • Pinnick oxidation • Aldehyde → CarboxAcid • Alkyl-OH → Aldehyde • O-C(O)R → O-H • O-H → O-C(O)R •
Reagents: Chiral auxiliary-Evans • Vinyl-MgX • CuBr·SMe2 • Allyl-SiR3 • BH4-Li+ • Carbodiimide • NBS • LiSnR3 • Allyl-SnR3 • Corey diazaborolidine • Chiral auxiliary-Boronate • Iodosobenzene-TFA • Me3O+ X- • OsO4, NMO • Periodate, sodium • AlH4-Li+ • H3PO4 • Acetic anhydride, DMAP • Butadiene, 2-OR • ZnCl2 • Chiral catalyst • Corey oxazaborolidine • BH3·THF • Acetic anhydride, Py • DDQ • Dess-Martin • Chlorite, sodium • NaOMe • Benzoyl chloride, 2,4,6-trichloro • DMAP • CuBr·SMe2 • Ephedrine • Allyl-BR2

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