⚠ 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 illiciumderived 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 latestage 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 OrthoBenzoquinones and Biomimetic Skeletal Rearrangement of AlloCedranes (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 13 (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)