How are you making that diene though?

Stereocontrolled organic synthesis of an intermediate used in the total synthesis of the cytotoxic marine macrolide aplyronine by the Paterson Group (Department of Chemistry, University of Cambridge). Many alternative organic chemistry concepts and options are evaluated for practicality on scale and for solving chemoselectivity problems. These are highlighted by retro synthetic analysis using a standard disconnection approach to retrosynthesis. Key steps in the chemistry include a boron aldol reaction, an Evans-Tishchenko reduction and a Trost alkyne to diene isomerisation. The aim of the video is to explain challenges in organic synthesis. LINKS and REFERENCES: Paterson Aplyronine Synthesis: I. Paterson, C. J. Cowden, M. D. Woodward, Tetrahedron Lett. 1998, 39, 6037–6040 https://doi.org/10.1016/S0040-4039(98... Org. Lett. 2013, 15, 12, 3118–3121 https://doi.org/10.1021/ol401327r Using TCA reagents for mild benzylation reactions:    • Retrosynthesis with Aldols   Boron-mediated aldol reactions with E enolates:    • Boron Aldol Reaction - Organic Chemistry, ...   1,3 hydroxyl directed reductions of ketones:    • Hydroxyl-directed 1,3 Reductions of Ketone...   Acetal formation mechanism:    • Acetal Formation - Organic Chemistry, Reac...   Trost Chemistry for alkyne to diene isomerisation: Isr. J. Chem. 2021, 61, 340 – 36 https://doi.org/10.1002/ijch.202000103 B. M. Trost, U. Kazmaier, J. Am. Chem. Soc. 1992, 114, 7933–7935 https://doi.org/10.1021/ja00046a062 #organicchemistry #science #chemistry