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. 2010 Nov 19;75(22):7869-76.
doi: 10.1021/jo101775n. Epub 2010 Oct 22.

A divergent strategy for the synthesis of secologanin derived natural products

Brandon J English  1 , Robert M Williams
Affiliations

A divergent strategy for the synthesis of secologanin derived natural products

Brandon J English et al. J Org Chem. .

Abstract

The syntheses of D,L-geissoschizol, D,L-corynantheidol, D,L-dihydrocorynantheol, D,L-protoemetinol, and D,L-3-epi-protoemetinol have been accomplished from a single synthetic intermediate.

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Figures

Figure 1
Figure 1
Target natural products.
Figure 2
Figure 2
Retrosynthetic analysis.
Scheme 1
Scheme 1
Biosynthesis of secologanin derived natural products.
Scheme 2
Scheme 2
Previous conversion of 6 to oleocanthal (7).
Scheme 3
Scheme 3
Synthesis of geissoschizol (8).
Scheme 4
Scheme 4
Selective reduction of lactone 6
Scheme 5
Scheme 5
Synthesis of corynantheidol (9).
Scheme 6
Scheme 6
Synthesis of dihydrocorynantheol (9).
Scheme 7
Scheme 7
Synthesis of 3-epi-protoemetinol (11).
Scheme 8
Scheme 8
Synthesis of protoemetinol (12).
See this image and copyright information in PMC

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