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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 7
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Original Articles

(+)-Cannabispirenone-A: Synthesis and Absolute Configuration

, , &
Pages 599-603 | Published online: 05 Dec 2006

References

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  • Johnson , M. R. and Milne , G. M. 1980 . J. Heterocyclic Chem. , 17 : 1817 As an example the analgetic activity of Nantradol resides in the levorotatory isomer
  • Raucher , S. and Koolpe , G. A. 1983 . J. Org. Chem. , 48 : 2066
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  • Nicolaou , K. C. , Magolda , R. L. and Claremon , D. A. 1980 . J. Am. Chem. Soc. , 102 : 1404 The best conditions for this homologation were those of Nicolaou The (E)- and (Z)- enol ethers are readily separable by PTLC. The (Z)-enol ether exhibited NMR: δ6.4, 1H; 6.3, 1H; 6.0, 1H; 4.0, s, 3H; 3.9, s, 3H; 3.75, s, 3H. Rf (SiO2, CH2Cl2) 0.3. The (E)-and (Z)-enol ethers also hydrolyze to the identical aldehyde. At 0°C the ratio of (Z)-and (E)- is 67:33
  • Seebach , D. , Kalinowski , H.-O. , Bastani , B. , Crass , G. , Daum , H. , Dorr , H. , DuPreez , N. P. , Ehrig , V. , Langer , W. , Nussler , C. , Oei , H.-A. and Schmidt , M. 1977 . Helv. Chim. Acta , 60 : 301 Prepared according to
  • Sone , T. , Terashima , S. and Yamada , S. 1976 . Chem. Pharm. Bull. , 24 : 1273
  • The ketoaldehyde (i) has m/z 276 (10% R.I.) 247 100. NMR: δ9.4, s
  • We acknowledge support of the M. J. Murdock Charitable Trust of Research Corporation, the Petroleum Research Fund administered by the American Chemical Society and the National Institutes of Health Biomedical Research Support Grant No. 2-S07-RR07170–06. We would also like to thank Xenia Kovacs of G. D. Searle and Co. for the ORD spectrum

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