Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 18
114
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

CONVENIENT SYNTHESIS OF RETINOL-RELATED POLYENES THROUGH HYDROXYALKYLATION OF 3-SULFOLENES

, &
Pages 2787-2793 | Received 28 Nov 2000, Published online: 15 Aug 2006

REFERENCES

  • Nicolaou , K. C. , Ramphal , J. Y. , Petasis , N. A. and Sehan , C. N. 1991 . Angew. Chem. , 30 : 1100 Int. Ed. Engl
  • Chemin , D. and Linstrumelle , G. 1992 . Tetrahedron , 48 : 1943
  • Alam , M. , Crousse , B. , Linstrumelle , G. , Mambu , L. and Larcheveque , M. 1993 . Synlett , 217 and references therein
  • Nicolaou , K. C. , Chakraborty , T. K. , Ogawa , Y. , Daines , R. A. , Simpkins , N. S. and Frust , G. T. 1988 . J. Am. Chem. Soc. , 110 : 4660
  • Rychousky , S. D. and Hoye , R. C. 1994 . J. Am. Chem. Soc. , 116 : 1753
  • Sporn , M. B. , Roberts , A. B. and Goodman , D. S. 1994 . The Retinoids; Biology and Chemistry, 2nd Edition 319 – 387 . New York : Raven Press .
  • Crousse , B. , Alami , M. and Linstrumelle , G. 1997 . Tetrahedron Lett. , 38 : 5297 and references therein
  • Chou , T. S. , Tao , H. H. and Chang , L. J. 1984 . Chem. Soc., Chem. Commun. , : 1323
  • Yamada , S. , Ohsawa , H. , Suzuki , T. and Takayama , H. J. 1986 . Org. Chem. , 51 : 4934
  • Padmakumar , R. , Subramanian , T. and Bhat , S. V. 1995 . Org. Prep. Proc. Int. , 27 : 463
  • Wingler , J. D. , Kim , H. S. and Kim , S. 1995 . Tetrahedron Lett. , 36 : 687
  • Chou , T. S. and Tso , H. H. 1989 . Org. Prep. Proc. Int. , 21 : 257 For reviews, see
  • Subramanian , T. , Padmakumar , R. and Bhat , S. V. 1997 . Tetrahedron Lett. , 32 : 2585
  • Desai , S. R. , Gore , R. G. , Mayelvaganan , T. , Padmakumar , R. and Bhat , S. V. 1992 . Tetrahedron , 48 : 481
  • Isler , O. , Huber , W. and Kofler , M. 1947 . Helv. Chim. Acta. , 30 : 1911
  • Isler , O. , Ronoco , A. , Guex , W. , Hindley , N. C. , Huber , W. , Dialer , K. and Kofler , M. 1949 . Helv. Chim. Acta , 32 : 489
  • Horing , E. C. Organic Synthesis . Collective , 3 499 – 500 .
  • Chou , T. S. , Tso , H. H. and Chang , L. J. 1984 . J. Chem. Soc., Chem. Commun. , 20 : 1323
  • The 2-benzyloxymethyl-3-methyl-3-sulfolene 1e was prepared by the reaction of the corresponding diene with sulfur dioxide at 80°C
  • Shantz , E. M. , Cawley , J. D. and Embree , N. D. 1943 . J. Am. Chem. Soc. , : 901
  • Mahiphal Reddy , A. and Jeyathirtha Rao , V. 1992 . J. Org. Chem. , 57 : 6727
  • All these polyenes are highly unstable in the presence of light at room temperature
  • IR spectra were run on a Perkin–Elmer model 681 and FT-IR spectrometers. 1H NMR spectra were recorded on Varian (300 MHz) and Brucker (300 MHz) spectrometers using CDCl3 with TMS as internal standard. Mass spectra were obtained on a Shimadzu QP-1000 mass spectrometer at 70 eV. UV spectra were recorded on Perkin–Elmer Lambda UV/VIS spectrometer. Silica gel (100–200 mesh) was used for column chromatography

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.