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. 2009 Jan 1;11(1):49-52.
doi: 10.1021/ol802329y.

Formal synthesis of (+/-)-roseophilin

Abdallah Y Bitar  1 , Alison J Frontier
Affiliations

Formal synthesis of (+/-)-roseophilin

Abdallah Y Bitar et al. Org Lett. .

Abstract

A formal synthesis of (+/-)-roseophilin is described. Scandium(III)-catalyzed Nazarov cyclization of 2,5-disubstituted N-tosylpyrrole 19 gives a 5,5'-fused ketopyrrole, and ansa-bridge formation via pi-allyl palladium macrocyclization gives 21.

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Figures

Figure 1
Figure 1
ORTEP drawing of macrocycle 21.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Scheme 5
Scheme 5
See this image and copyright information in PMC

References

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    1. For applications of different Nazarov cyclization strategies toward roseophilin, see references 4f, 4j, 4k and 4m.

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