⚠️ This video contains advanced organic chemistry!
Illisimonin A is the perfect quest for synthesis practicioners – it is bioactive (neurotrophic), structurally complex and highly oxygenated. This video will explain the isolation of this illicium-derived natural product and properties. Two modern syntheses (2019 and 2023) will be discussed, highlighting unique approaches and common methodologies to access this interesting target.
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00:00 Why we should care about illicium natural products
00:47 How it was discovered, isolated and characterized
01:40 The property that makes it exciting¨
02:49 Retrosynthetic analysis and key late-stage disconnections
04:53 Rychnovsky: First total synthesis (racemic) and structural revision
08:29 Kalesse: Asymmetric total synthesis
13:43 Closing remarks
Key references:
– Asymmetric Total Synthesis of Illisimonin A (J. Am. Chem. Soc. 2023, 145, 7021)
– Total Synthesis and Structure Revision of (−)-Illisimonin A, a Neuroprotective Sesquiterpenoid from the Fruits of Illicium simonsii (J. Am. Chem. Soc. 2019, 141, 13295)
– Illisimonin A, a Caged Sesquiterpenoid with a Tricyclo[5.2.1.01,6]decane Skeleton from the Fruits of Illicium simonsii (Org. Lett. 2017, 19, 6160)
– Other related publication: Synthesis of Illisimonin a Skeleton by Intramolecular Diels–Alder Reaction of Ortho-Benzoquinones and Biomimetic Skeletal Rearrangement of Allo-Cedranes (Organics 2021, 2, 306)
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)
