Total synthesis of Endiandric acids:
| Reference: | Nicolaou, K. C.; Petasis, N. A.; Zipkin, R. E. J. Am. Chem. Soc. 1982, 104, 5558, DOI 5560. DOI |
| Reactions: | O-SiMe2tBu → O-H • Sulfide → Sulfoxide • Sulfide → Sulfoxide • Li-Allenyl/Propargyl+Alkyl-X • Alkyl-X+Li-R • HWE → EnoateEster • HWE → Diene • Sulfoxide-Ei → Enyne • Alkyne → Ene-cis (Lindlar) • Sulfoxide-Ei → Enyne • Si-Alkynyl → H-Alkynyl • Diels-Alder, Intram, Ene • Bicyclo(420) • Bicyclo(222) • Electrocyclic-8π • Cyclooctane • Electrocyclic-6π • Cyclobutane • Cyclohexene • Bicyclo(420) • Alkyl-OH → Aldehyde • CompOx-Alkyl-OH/Sulfide+CrO3 • Glaser coupling • Si-Alkynyl → H-Alkynyl • |
| Reagents: | LiNiPr2 • CrO3Cl·PyH (PCC) • P(O)(OR)2CH2-C(O)OR' • NaH • Acetic acid • Perbenzoic acid, 3-chloro • AgNO3 • Cu(OAc)2 • AgNO3 • Perbenzoic acid, 3-chloro • H2, Pd • Cyanide, potassium • P(O)(OR)2CH2-Vinyl • LiNiPr2 • |