Total synthesis of Nakadomarin A (Evans):
| Reference: | Bonazzi, S.; Cheng, B.; Wzorek, J. S.; Evans, D. A. J. Am. Chem. Soc. 2013, 135, 9338-9341 DOI |
| Reactions: | Li-Aryl → I-Aryl • CarboxEster → CarboxAcid • Pd-Heck coupling • Wittig-alkyl → Ene-cis • HWE → EnoateEster-cis • Sulfinamide, chiral • Acetal → Aldehyde • N-H → N-Alkyl • RCM → Ring-N • Amine-8 • Bicyclo(630)-aza • Aldehyde protection • Li/H → Li-Furyl • ConjAdd Amine • ConjAdd EnolSilane • Lactam-6 • Friedel-Crafts Acylation • Iminium → Amine • Zn-Allyl+Imine • Imine+M-R • Mechanism • Aldehyde → Acetal(Me) • CarboxEster → CarboxAcid • N-Boc → N-H • CarboxAcid → CarboxAmide • Lactam-9+ • Paracyclophane • N-S(O)R → N-H • Lactam-5 • Lactam-5 • |
| Reagents: | HO-Allyl • BuLi(n) • BuLi(sec) • I2 • TsOH • Pd(OAc)2 • KN(SiMe3)2 • KN(SiMe3)2 • 18-crown-6 • Hydroxide, sodium • Acetic acid, trifluoro • HBTU • Pyridine, 2,6-di-tBu • Tf2O • Allyl-ZnX • Hydroxide, sodium • NaH • Grubbs I • PPh3 • Chiral auxiliary (sulfinamide) • P(O)(OCH2CF3)2CH2-C(O)OMe • NEtiPr2 • SiMe2tBu-OTf • AlH2(OR)2-Na+ • Furyl-Li • HCl, H2O • Sulfinamide • DMF (solvent) • Morpholine • |