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Multicomponent coupling approach to (+/-)-frondosin B and a ring-expanded analogue.
Daniel J Kerr1, Anthony C Willis, Bernard L Flynn
1Department of Chemistry and The Research School of Chemistry, Australian National University, Canberra, ACT, 0200, Australia. bernard.flynn@vcp.monash.edu.au
Organic Letters
|February 14, 2004
Summary
A new multicomponent coupling reaction provides direct access to a key frondosin B intermediate. This intermediate can be converted into a ring-expanded analogue via heating, involving a novel tandem hydrogen shift and electrocyclization.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Frondosin B is a natural product with potential biological activity.
- Efficient synthesis of complex molecules like frondosin B is a significant challenge in organic chemistry.
Purpose of the Study:
- To develop a novel multicomponent coupling reaction for synthesizing a late-stage intermediate of frondosin B.
- To explore the conversion of this intermediate into a ring-expanded analogue.
Main Methods:
- Utilized a recently discovered multicomponent coupling reaction.
- Employed sustained heating to induce a reaction in the synthesized intermediate.
Main Results:
- Direct access to a late intermediate in frondosin B synthesis was achieved.
- Efficient conversion to a ring-expanded analogue of frondosin B was observed.
- An unprecedented tandem 1,7-hydrogen shift and 8pi-electrocyclization mechanism was proposed for the analogue formation.
Conclusions:
- The developed multicomponent coupling reaction offers an efficient route to frondosin B intermediates.
- The study reveals a novel pathway for generating ring-expanded analogues through thermal rearrangement.
- The proposed tandem reaction mechanism provides new insights into complex molecular transformations.