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. 2010 Mar 19;12(6):1244-7.
doi: 10.1021/ol100113r.

A tandem Prins/Schmidt reaction approach to marine alkaloids: formal and total syntheses of lepadiformines A and C

Angelica M Meyer  1 , Christopher E Katz, Sze-Wan Li, David Vander Velde, Jeffrey Aubé
Affiliations

A tandem Prins/Schmidt reaction approach to marine alkaloids: formal and total syntheses of lepadiformines A and C

Angelica M Meyer et al. Org Lett. .

Abstract

The tricyclic core of the cylindricine or lepadiformine families of alkaloid natural products was assembled via a Prins addition/intramolecular Schmidt rearrangement under Lewis acid conditions. Both single-pot and two-stage variations of this process were examined, with particular attention to the stereochemical outcome of the processes. This technology has been applied to a formal total synthesis of lepadiformine A and a total synthesis of lepadiformine C.

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Figures

Figure 1
Figure 1
Representative Structures from the Genus Clavelina
Scheme 1
Scheme 1
Retrosynthetic Analysis of Cylindricine C
Scheme 2
Scheme 2
Prins Precedent
Scheme 3
Scheme 3
Two-Step Prins/Schmidt Reaction Sequence
Scheme 4
Scheme 4
Reaction of 4 and a β-Substitued Azidoacetal
Scheme 5
Scheme 5
Tandem Prins/Schmidt Reaction with 3-Azidopropanal
Scheme 6
Scheme 6
Stereochemical Effect on Reaction Products From the Tandem Reaction of 4 and 12
Scheme 7
Scheme 7
Tandem Prins/Schmidt Reaction with β-Substituted Azidoaldehydes
Scheme 8
Scheme 8
Formal Synthesis of Lepadiformine A
Scheme 9
Scheme 9
Total Synthesis of Lepadiformine C
See this image and copyright information in PMC

References

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