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. 2012 Apr 20;14(8):2110-3.
doi: 10.1021/ol300647k. Epub 2012 Apr 3.

Synthesis of the bridging framework of phragmalin-type limonoids

Terry P Lebold  1 , Gary M Gallego, Christopher J Marth, Richmond Sarpong
Affiliations

Synthesis of the bridging framework of phragmalin-type limonoids

Terry P Lebold et al. Org Lett. .

Abstract

An efficient synthesis of the octahydro-1H-2,4-methanoindene core of phragmalin-type limonoids, such as xyloccensins O and P, is reported. The success of the synthetic route is predicated on the use of network analysis in the retrosynthetic analysis and a Diels-Alder reaction for the synthesis of a key hydrindanone derivative.

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Figures

Figure 1
Figure 1
Selected limonoid natural products
Figure 2
Figure 2
ORTEP representation of 22
Scheme 1
Scheme 1
Proposed biogenetic connection between mexicanolide-type and phragmalin-type limonoids
Scheme 2
Scheme 2
Retrosynthetic analysis of 14
Scheme 3
Scheme 3
Synthesis of diene 12
Scheme 4
Scheme 4
Synthesis of hydrindanone derivative 13
Scheme 5
Scheme 5
Fragmentation pathway of 14
Scheme 6
Scheme 6
Michael addition
See this image and copyright information in PMC

References

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