Total synthesis of Spinosyn A Nucleus:
| Reference: | Mergott, D. J.; Frank. S. A.; Roush, W. R. Org. Lett. 2002, 4, 3157. DOI |
| Reactions: | EnoateEster → Allyl-OH • Allyl-OH → Enal • O-SiMe2tBu → O-H • HWE → EnoateEster-cis • HWE → EnoateEster • Wittig-ketomethyl → Enone • Pd/B-Vinyl+Vinyl-X • Barton-McCombie reduction • Diels-Alder, Intram, Ene • Cyclopentane • Bicyclo(430) • Morita-Bayliss-Hillman • Cyclopentene • Bicyclo(430) • Aldol-Base → EnoateEster • O-H → O-C(S)NR2 • Allyl-OH → Enal • Vinyl-Br → Vinyl-H • |
| Reagents: | P(O)(OR)2CH2-C(O)OR' • DBU • AlHiBu2 • Dess-Martin • PPh3=CH-COMe • Pd(PPh3)4 • Dess-Martin • P(O)(OCH2CF3)2CH2-C(O)OMe • KN(SiMe3)2 • HF·Py • HSi(SiMe3)3 • AIBN • S=C(Imid)2 • AlMeCl2 • PMe3 • Vinyl-BR2 • |