Total synthesis of HPA-12:
| Reference: | Snider, J. R.; Entrekin, J. T.; Snowden, T. S.; Dolliver, D. Synthesis 2013, 45, 1899-1903. DOI |
| Reactions: | Friedel-Crafts Acylation • Ketone → Alkyl-OH • Felkin-Anh Chelation • Epoxidation via halohydrin • Epoxide+M-N3 • Lactone-5 • N-H → N-C(O)R • Staudinger • Mechanism • Lactone → Alkyl-OH • |
| Reagents: | AlCl3 • BH(OAc)3-Me4N+ • Acetic acid • PPh3 • BH4-Na+ • Hydroxide, sodium • Azide, sodium • |