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An organic chemistry minilecture on ’A Convergent Total Synthesis of ( )-Ineleganolide’ by Benjamin M. Gross, Seo-Jung Han, Scott C. Virgil, and Brian M. Stoltz*. The synthesis is the culmination of over two decades of research and features a creative allylic transposition, an aldol cyclization cascade and a stereoselective semipinacol rearrangement.
ERRATUM: AT 5:10 the formula for oxalyl chloride should read (COCl)2, not COCl2
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References:
J. Am. Chem. Soc. 2023, 145, 7763−7767 (This work)
Tetrahedron Lett. 1999, 40, 6033−6035 (Isolation)
J. Am. Chem. Soc. 2022, 144, 20539−20547 (Wood Synthesis)
Chem. Sci., 2017,8, 507-514 (Previous work towards ineleganolide)
Science 2016, 352, 1078−1082 (Precursor Synthesis)
JACS. 2022, 144, 20232−20236 (Precursor Synthesis)
J. Org. Chem. 73, 12, 2008 (Carvone rearrangement)
R. Soc. Open Sci. 2018, 5, 171988 (TPPO Esterification)
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