Total Synthesis of Ineleganolide

To try everything Brilliant has to offer—free—for a full 30 days, visit . The first 200 of you will get 20% off Brilliant’s annual premium subscription. 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 SUPPORT THE CHANNEL ON PATREON: NMR Spectroscopy in music: J. New Music Res. 2021, 50:5, 487-501 Socials: 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) This video was sponsored by Brilliant