Total synthesis of Laurencin:
| Reference: | Krüger, J.; Hoffmann, R. W. J. Am. Chem. Soc. 1997, 119, 7499. DOI |
| Reactions: | O-H → O-Allyl • Wittig-alkyl → Ene-cis • Protecting group - CarboxAcid • Li/H → Li-Allyl • Li-R → B-R • CarboxAmide(Weinreb) → Aldehyde • B-Allyl+Aldehyde • Ether-8 • Protecting group - Aldehyde • Alkyl-OH → Aldehyde • CarboxAcid → CarboxAmide(Weinreb) • Alkyl-OH → Aldehyde • Orthoester → CarboxEster • CarboxEster → CarboxAcid • |
| Reagents: | Acetonitrile, trichloro • AlH4-Li+ • Dess-Martin • PPh3=CH-Alkyl • Bisulfate, sodium • Hydroxide, lithium • Carbodiimide • NHMe(OMe) • AlHiBu2 • BuLi(sec) • B(OR)3 • Allyl-BR2 • |