Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol.

Russell, David A; Freudenreich, Julien J; Stewart, Hannah L; Bond, Andrew D; Sore, Hannah F; Spring, David R

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Authors

Russell, David A

Freudenreich, Julien J

Stewart, Hannah L

Bond, Andrew D

Sore, Hannah F

Spring, David R

Publication Date

2018-09-11

Journal Title

Org Biomol Chem

ISSN

1477-0520

Publisher

Royal Society of Chemistry (RSC)

Volume

Issue

Pages

6395-6398

Language

eng

Type

Article

Physical Medium

Metadata

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Citation

Russell, D. A., Freudenreich, J. J., Stewart, H. L., Bond, A. D., Sore, H. F., & Spring, D. R. (2018). Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol.. Org Biomol Chem, 16 (35), 6395-6398. https://doi.org/10.1039/c8ob01919c

Abstract

We describe semi-syntheses of the 11-hydroxyrotenoids sumatrol (1) and villosinol (2), starting from rotenone (5), using an oxime-directed C11-H functionalisation approach. Thus, rotenone (5) was converted into rotenone oxime (6), which gave dimeric palladacycle 7 following reaction with Na2PdCl4·3H2O. Controlled, divergent, oxidation of palladacycle 7 with either Pb(OAc)4 or K2Cr2O7 afforded the 11-acetoxylated intermediates 9 and 13, respectively, which were transformed into sumatrol (1) and villosinol (2).

Keywords

0601 Biochemistry and Cell Biology

Sponsorship

Engineering and Physical Sciences Research Council (EP/J016012/1)

Engineering and Physical Sciences Research Council (EP/P020291/1)

Identifiers

External DOI: https://doi.org/10.1039/c8ob01919c

This record's URL: https://www.repository.cam.ac.uk/handle/1810/285443

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