(+)-Milbemycin β3(1) was prepared by total synthesis from (6S,8R,9S)-methyl 8,9-dimethyl-4-oxo-1,7-dioxaspiro[5.5]undeco-2-ene-2-carboxylate (2), (4R,6R)-4-methyl-6-phenylsulphonyl-(E)-hept-2-en-1-ol (3a), and 2-ethyl-4-methoxy-5-methylbenzoic acid (4) using Julia–Lythgoe and benzylic anion chemistry to establish the carbon framework and a Mitsunobu reaction to close the lactone ring.
S. V. Attwood, A. G. M. Barrett, R. A. E. Carr and G. Richardson, J. Chem. Soc., Chem. Commun., 1986, 479 DOI: 10.1039/C39860000479
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