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Total synthesis of Spinosyn A Nucleus:
Reference: Mergott, D. J.; Frank. S. A.; Roush, W. R. Org. Lett. 2002, 4, 3157. DOI
Keywords: EnoateEster → Allyl-OH • Allyl-OH → Enal • 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 • Cyclopentane • Morita-Bayliss-Hillman • Cyclopentene • O-H → O-C(S)NR2
Reagents: P(O)(OR)2CH2-C(O)OR' • DBU • AlHiBu2 • Dess-Martin • PPh3=CH-COMe • Vinyl-BR2 • Pd(PPh3)4 • Dess-Martin • P(O)(OCH2CF3)2CH2-CO2Me • KN(SiMe3)2 • HF·Py • HSi(SiMe3)3 • AIBN • S=C(Imid)2 • AlMeCl2 • PMe3

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