Synthesis of Spiro[4.5]decan-1-ones: A Formal Synthesis of Acoradienes and Related Sesquiterpenes via Rhodium-catalyzed Claisen Rearrangement/Hydroacylation

Synlett ◽  
1996 ◽  
Vol 1996 (12) ◽  
pp. 1221-1223 ◽  
Author(s):  
Tim Sattelkau ◽  
Christoph Hollmann ◽  
Peter Eilbracht
Keyword(s):  
Claisen Rearrangement ◽  
Formal Synthesis

Total synthesis of Sceletium alkaloids (±)-joubertinamine, (±)-epijoubertinamine, (±)-tortuosamine and formal synthesis of (±)-mesembrine, (±)-N-formyltortuosamine

2016 ◽  
Vol 40 (11) ◽  
pp. 9432-9440 ◽  
Author(s):  
Viraj A. Bhosale ◽  
Dattatraya U. Ukale ◽  
Suresh B. Waghmode
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Formal Synthesis ◽  
Wittig Olefination

An efficient collective formal/total synthesis of Sceletium alkaloids achieved by employing the Wittig olefination–Claisen rearrangement protocol.

scholarly journals Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins Allowing a Formal Synthesis of Trichoderone A

2021 ◽  
Author(s):  
Oscar Gayraud ◽  
Benjamin Laroche ◽  
Nicolas Casaretto ◽  
Bastien Nay
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
Two Phase ◽  
Formal Synthesis ◽  
Diels Alder Reaction ◽  
Oxidative Transformations ◽  
High Degree

Aspochalasins are leucine-derived cytochalasins. Their complexity is often associated to a high degree of biosynthetic oxidative transformations that could inspire a two-phase strategy in total synthesis. In that context, we describe the synthesis of a putative biomimetic tetracyclic intermediate. The key constructive steps are an intramolecular Diels-Alder reaction to install the characteristic isoindolone core of cytochalasins, whose branched precursor was obtained from a stereoselective Ireland-Claisen rearrangement made on a highly unsaturated substrate. This work also constitutes a formal synthesis of trichoderone A.

Transannular Claisen rearrangement reactions for the synthesis of vinylcyclobutanes: formal synthesis of (±)-grandisol

2011 ◽  
Vol 9 (23) ◽  
pp. 8000 ◽  
Author(s):  
Donald Craig ◽  
Kiyohiko Funai ◽  
Sophie J. Gore ◽  
Albert Kang ◽  
Alexander V. W. Mayweg
Keyword(s):  
Claisen Rearrangement ◽  
Formal Synthesis ◽  
Rearrangement Reactions

scholarly journals Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins Allowing a Formal Synthesis of Trichoderone A

2021 ◽  
Author(s):  
Oscar Gayraud ◽  
Benjamin Laroche ◽  
Nicolas Casaretto ◽  
Bastien Nay
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
Two Phase ◽  
Formal Synthesis ◽  
Diels Alder Reaction ◽  
Oxidative Transformations ◽  
High Degree

Aspochalasins are leucine-derived cytochalasins. Their complexity is often associated to a high degree of biosynthetic oxidative transformations that could inspire a two-phase strategy in total synthesis. In that context, we describe the synthesis of a putative biomimetic tetracyclic intermediate. The key constructive steps are an intramolecular Diels-Alder reaction to install the characteristic isoindolone core of cytochalasins, whose branched precursor was obtained from a stereoselective Ireland-Claisen rearrangement made on a highly unsaturated substrate. This work also constitutes a formal synthesis of trichoderone A.

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