Semi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol
Literature Information
Publication Date
2018-08-22
DOI
10.1039/C8OB01919C
Impact Factor
3.876
Authors
David A. Russell, Julien J. Freudenreich, Hannah L. Stewart, Andrew D. Bond, Hannah F. Sore, David R. Spring
View Original
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).
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
2-(2-Aminoethyl)-1H-isoindole-1,3(2H)-dione hydrochloride (1:1)
CAS Number:
30250-67-0
Molecular Formula:
C10H11ClN2O2
![N,N'-1,2-Ethanediylbis[2-(vinylsulfonyl)acetamide] structure](https://static.chemtradehub.com/structs/667/66710-66-5-b556.webp "N,N'-1,2-Ethanediylbis[2-(vinylsulfonyl)acetamide] structure")
N,N'-1,2-Ethanediylbis[2-(vinylsulfonyl)acetamide]
CAS Number:
66710-66-5
Molecular Formula:
C10H16N2O6S2
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