🧠 The chemists who discovered pagodane described it simply but accurately: this is a highly complex, aesthetically appealing molecule. In this video, you will see how Prinzbach and co-workers used quite straight-forward chemical reactions to synthesize the impressive pagodane, leveraging symmetry and inherent reactivity. Also, we will learn how it's connected to the isomer dodecahedrane and the unique case of sigma-bishomoaromaticity present in one of its derivatives.

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00:00 Pagodane and chemical synthesis of complex frameworks & natural products
01:04 Context on pagodane's synthesis: Aldrin and isodrin, potent insecticides
02:08 Prinzbach's forward synthesis of pagodane
05:16 Dodecahedrane synthesis from pagodane
07:11 Sigma-homobisaromaticity of a cyclobutanoid system in pagodane

References:
- "Pagodane": the efficient synthesis of a novel, versatile molecular framework: J. Am. Chem. Soc. 1987, 109, 15, 4626
- Stable carbocations. Part 267. Pagodane dication, a unique 2.pi.-aromatic cyclobutanoid system: J. Am. Chem. Soc. 1986, 108, 4, 836
- From an Insecticide to Plato's Universe—The Pagodane Route to Dodecahedranes: New Pathways and New Perspectives: Angew. Chem. Int. Ed. Engl. 1994, 33, 2239
- Dodecahedrane: J. Am. Chem. Soc. 1982, 104, 16, 4503

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Some recommended books on organic synthesis:
- Clayden, Greeves, Warren; Organic Chemistry (basic organic chemistry knowledge)
- Wyatt, Warren; Organic Synthesis: The Disconnection Approach (excellent introduction to retrosynthesis)
- Kurti, Czako; Strategic Applications of Named Reactions in Organic Synthesis (extensive toolkit of functional group reactions and applications thereof with common conditions)
- Nicolaou; Classics in Total Synthesis 1-3 (the ultimate total synthesis trilogy)
- Nicolaou; Molecules That Changed the World (the world's most important molecules and their impact on everyday life)
- Carreira, Kvaerno; Classics in Stereoselective Synthesis (compilation of the groundbreaking methods of stereoselective synthesis and application to synthesis of stereochemically complex structures)