Synthetic Route to an Aromatic Analog of Strigol
Publication
, Journal Article
Kendall, PM; Johnson, JV; Cook, CE
Published in: Journal of Organic Chemistry
January 1, 1979
An aromatic analogue which contains all but one of the carbon atoms of the witchweed seed germination stimulant strigol has been prepared. 6-Methyldihydrocoumarin was converted to a phenolic indanone (4) which was alkylated by reaction of its dianion with lithium bromoacetate. Reduction and acid treatment yielded a lactone (7) which (as its tert- butyldimethylsily 1 derivative) was converted to the hydroxymethylene compound 9. The sodium salt of 9 underwent O-alkylation with bromolactone 10 to yield the protected strigol and epistrigol analogues 11. Removal of the silyl ether was effected with aqueous fluoride at pH 5. © 1979, American Chemical Society. All rights reserved.
Duke Scholars
Published In
Journal of Organic Chemistry
DOI
EISSN
1520-6904
ISSN
0022-3263
Publication Date
January 1, 1979
Volume
44
Issue
9
Start / End Page
1421 / 1424
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
Citation
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MLA
NLM
Kendall, P. M., Johnson, J. V., & Cook, C. E. (1979). Synthetic Route to an Aromatic Analog of Strigol. Journal of Organic Chemistry, 44(9), 1421–1424. https://doi.org/10.1021/jo01323a013
Kendall, P. M., J. V. Johnson, and C. E. Cook. “Synthetic Route to an Aromatic Analog of Strigol.” Journal of Organic Chemistry 44, no. 9 (January 1, 1979): 1421–24. https://doi.org/10.1021/jo01323a013.
Kendall PM, Johnson JV, Cook CE. Synthetic Route to an Aromatic Analog of Strigol. Journal of Organic Chemistry. 1979 Jan 1;44(9):1421–4.
Kendall, P. M., et al. “Synthetic Route to an Aromatic Analog of Strigol.” Journal of Organic Chemistry, vol. 44, no. 9, Jan. 1979, pp. 1421–24. Scopus, doi:10.1021/jo01323a013.
Kendall PM, Johnson JV, Cook CE. Synthetic Route to an Aromatic Analog of Strigol. Journal of Organic Chemistry. 1979 Jan 1;44(9):1421–1424.
Published In
Journal of Organic Chemistry
DOI
EISSN
1520-6904
ISSN
0022-3263
Publication Date
January 1, 1979
Volume
44
Issue
9
Start / End Page
1421 / 1424
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry