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Total synthesis of Nakadomarin A:
Reference: Bonazzi, S.; Cheng, B.; Wzorek, J. S.; Evans, D. A. J. Am. Chem. Soc. 2013, 135, 9338-9341 DOI
Keywords: Li-Aryl → I-Aryl • Aldehyde → Acetal(Me) • CarboxEster → CarboxAcid • N-Boc → N-H • CarboxAcid → CarboxAmide • N-S(O)R → N-H • CarboxEster → CarboxAcid • Pd-Heck coupling • Wittig-alkyl → Ene-cis • HWE → EnoateEster-cis • Sulfinamide, chiral • N-H → N-Alkyl • RCM → Ring-N • Aldehyde protection • Li/H → Li-Furyl • ConjAdd Amine • ConjAdd EnolSilane • Friedel-Crafts Acylation • Iminium → Amine • Zn-Allyl+Imine • Imine+Zn-R • Mechanism •
Reagents: Chiral auxiliary-Sulfox • Sulfinamide • BuLi(n) • BuLi(sec) • TsOH • Pd(OAc)2 • KN(SiMe3)2 • KN(SiMe3)2 • 18-cr-6 • Hydroxide, sodium • Acetic acid, trifluoro • HBTU • Tf2O • AlH2(OR)2-Na+ • Allyl-ZnX • HCl, H2O • Hydroxide, sodium • NaH • Grubbs I • PPh3 • HCl • P(O)(OCH2CF3)2CHR-CO2Me • NEtiPr2 • SiMe2tBu-OTf •

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