Total Synthesis (E) and (Z)‑Ocellenyne

An organic chemistry minilecture on the ’Total Synthesis and Structure Confirmation of (E) and (Z)‑Ocellenyne’ by Harry B. Hicks, Daniel S. Brown, Hau Sun Sam Chan, Bruno A. Sousa, Kirsten E. Christensen, Jonathan W. Burton*. Highlights include a tandem Sakurai/deacetylation, a Colvin homologation and a deboronoiodination to form a Z-vinyliodide SUPPORT THE CHANNEL ON PATREON: NMR Spectroscopy in music: J. New Music Res. 2021, 50:5, 487-501 Socials: References: Org. Lett. 2022 24 (50), 9174-9178 (This work) J. Org. Chem. 1981, 46, 19, 3870–3873 (Discovery) J. Am. Chem. Soc. 2019, 141, 40, 15951–15962 (dehydroglucose SM) Org. Lett. 2001, 3, 16, 2513–2515 (Diol Epoxidation) Inorg. Chem. 1964, 3, 12, 1783–1785 (Nickel Boride Catalyst Structure) Tet. Lett. 1984, 25, 1631-1632 (in situ generation of BF3) J. Am. Chem. Soc. 2014, 136, 38, 13355–13362 (Halenium affinity scale) Synlett 1994, 2, 107-108 (Colvin Homologation) J. Am. Chem. Soc. 2021, 143, 2097−2107 (Colvin Homologation) J. Am. Chem. Soc. 1973, 95, 19, 6456–6457 (Z vinyl iodide formation) J. Org. Chem. 1989,54,6068-6075 (Z vinyl iodide formation) J. Org. Chem. 2003,68, 6031-6034 (Z vinyl iodide formation) ,43, 4704 (Stille Reaction Mechanism)