Total synthesis of Antibiotic X-14547A (partial):
| Reference: | Nicolaou, K. C. ; Papahatjis, D. P.; Claremon, D. A.; Dolle, R. E., III J. Am. Chem. Soc. 1981, 103, 6967. DOI |
| Reactions: | SAMP hydrazone • HWE → DienoateEster • Aldehyde azaenolate (asym)+Alkyl-X • Alkyl-X+Azaenolate • Wittig-carboxymethyl → EnoateEster • O-SiMe2tBu → O-H • CompE+-Si-O/Si-O+H2O • Ozonolysis C=N • Diels-Alder, Intram, Ene • Cyclopentane • Bicyclo(430) • EnoateEster → Allyl-OH • O-H → O-SiPh2tBu • Alkyl-OH → Aldehyde • |
| Reagents: | Chiral auxiliary (hydrazone-SAMP) • LiNiPr2 • AlHiBu2 • PPh3=CH-CO2R • SiPh2tBu-Cl • CrO3Cl·PyH (PCC) • O3 • P(O)(OR)2CH2-Vinyl • |