The Synthesis Of a 3,5-Cyclosteroidal Aldehyde from the Distillates of Canola Oil

References

• Dreier , S. and Towers , G. H. N. 1988 . J. Plant Physiol. , 132 : 509
   Web of Science ®Google Scholar
• Mitchell , J. W. , Mandava , N. , Worley , J. F. , Plimmer , J. R. and Smith , M. 1970 . Nature. , 225 : 1065
   PubMed Web of Science ®Google Scholar
• Worley , J. F. and Mitchell , J. 1971 . Amer. Soc. Hort Sci. , 96 : 270
   Web of Science ®Google Scholar
• Mitchell , J. W. and Gregory , L. E. 1972 . Nature , 222 : 253
   Google Scholar
• Maugh , T. H. 1981 . Science , 212 : 33
   PubMed Web of Science ®Google Scholar
• Yopp , J. H. , Mandava , N. B. and Sasse , J. M. 1981 . Physiol. Plant. , 53 : 445
   Web of Science ®Google Scholar
• Gregory , L. E. 1961 . Amer. J. Bot. , 68 : 586
   Google Scholar
• Takalsuto , S. , Ying , B. , Morisaki , M. and Ikekawa , N. 1982 . J. of Chrom. , 239 : 233
   Web of Science ®Google Scholar
• Grove , M. D. , Spencer , G. F. , Rohwedder , W. K. , Mandava , N. , Worley , J. F. , Warthen , J. D. , Steffens , G. L. , Flippen-Andereon , J. L. and Cook , J. C. 1979 . Nature , 281 : 216
   Web of Science ®Google Scholar
• Takematsu , T. , Ikekawa , N. and Shida , A. Eur. Pat Appl. EP . 218,945 . 1987 .
   Google Scholar
• Hamada , K. 1986 . FFTC BookSer. , 34 : 188
   Google Scholar
• Choi , C. , Takeuchi , Y. and Takematsu , T. 1986 . Shokubutsu no Kagaku Chosetsu , 21 : 134
   Google Scholar
• Takematsu , T. and Izumi , K. Jpn. Kokai Tokkyo Koho JP . 6204205 . 1987 .
   Google Scholar
• Jpn. Kokai Tokkyo Koho JP . 6267006 . 1987 . National Fed. of Agric. Co-Op. Assoc.
   Google Scholar
• Hirai , Y. and Fujii , S. Jpn. Kokai Tokkyo Koho JP . 6267005 . 1987 .
   Google Scholar
• Takahara , T. , Hirose , K. , Ono , Y. , Iwagaki , I. and Hirai , Y. Jpn. Kokai Tokkyo Koho JP . 6263501 . 1987 .
   Google Scholar
• Abe , H. , Morishita , T. , Uchiyama , M. , Marumo , S. , Manakata , K. , Takatsuto , S. and Ikekawa , N. 1982 . Agric. Biol. Chem. , 46 : 2609
   Web of Science ®Google Scholar
• Ikekawa , N. , Takatsuto , S. , Marumo , S. , Abe , H. N. , Morishita , T. , Uchiyama , M. , Ikeda , M. , Sasa , T. and Kitsuwa , T. 1983 . Proc. Jpn. Acad. Ser. B. , 59 : 9
   Web of Science ®Google Scholar
• Morishita , T. , Abe , H. , Uchiyama , M. , Marumo , S. , Takatsuto , S. and Ikekawa , N. 1983 . Phytochem. , 22 : 1051
   Web of Science ®Google Scholar
• Ikeda , M. , Takatsuto , S. , Sasa , T. , Ikekawa , N. and Nukina , M. 1983 . Agric. Biol. Chem. , 47 : 655
   Web of Science ®Google Scholar
• Sakakibara , M. , Okada , K. , Ichikawa , Y and Mori , K. 1982 . Hetarocycles. , 17 : 301
   Web of Science ®Google Scholar
• Mori , K. , Sakakibara , M. , Ichikawa , Y. , Ueda , H. , Okada , K. , Umemura , T. , Yabuta , G. , Kuwahara , S. , Kondo , M. , Minobe , M. and Sogabe , A. 1982 . Tet. , 38 : 2099
   Web of Science ®Google Scholar
• Sakakibara , M. and Mori , K. 1882 . Agric. Biol. Chem. , 47 : 663
   Google Scholar
• Mori , K , Sakakibara , M. and Okada , K. 1984 . Tel. , 40 : 1767
   Google Scholar
• Mori , K. 1985 . Rev. Latinoamer. Quim. , 16 : 55
   Google Scholar
• Mori , K . 1985 . Rev. Latinoamer. Quim. , 16 : 55
   Google Scholar
• Aburatani , M. , Takeuchi , T. and Mori , K. 1986 . Agric. Biol. Chem. , 50 : 3043
   Web of Science ®Google Scholar
• Aburatani , M. , Takeuchi , T. and Mori , K . 1987 . Synth. Comm. , : 181
   Web of Science ®Google Scholar
• Takatsulo , S. and Ikekawa , N. 1086 . Chem Pharm Bull , 34 : 1415
   Google Scholar
• Takatsuto , S. , Yazawa , N. , Ishiguro , M. , Morisaki , M. and Ikekawa , N. 1984 . J. Chem Soc , P1 : 139
   Google Scholar
• Donaubauer , J. R. , Greaves , A. M. and McMorris , T. C. 1984 . J. Org. Chem. , 49 : 2834
   Web of Science ®Google Scholar
• Mandava , N. B. 1988 . Ann. Rev. Physiol. Mol. Biol. , 39 : 23 and references therein.
   Web of Science ®Google Scholar
• Adam , G. and Marquardt , V. 1986 . Phytochemistry , 25 : 1787 and references therein. For syntheses Involving the starting materials stigmasterol, ergosterol, pregnenolone, dinorcholenic acid or 22-dehydrocampesterol:
   Web of Science ®Google Scholar
• Kircher , H. W. and Rosenstein , F. U. 1973 . Lipids , 8 : 453
   PubMed Web of Science ®Google Scholar
• Fieser , L. F. 1963 . Org. Syn. Coll. , 4 : 195
   Google Scholar
• A 585 ml(0.13 gallon) sample of canola oil distillate weighed 527 grams.
   Google Scholar
• Kindly donated by CSP Foods, Altona, Manitoba, Canada.
   Google Scholar
• Calculated by comparing the intensities of the 13C vinylic methane resonances of satunited(C6 at 125.6 ppm) and uneaturaled sterols(C22 at 131.7 ppm).
   Google Scholar
• This procedure was equally successful on a 90 gram scale of the canola derived phytosterols but required longer reaction times. It should be noted that the overall yield of this procedure has not been optimized since the SN 2 products 4 can be deprotected to the corresponding sterols and carried forward to aldehyde 5.
   Google Scholar
• As a comparison, the previous method15 would produce approximately 0.15 grams of brassicasterol 2 from 58 grams of canola oil distillate Given 85% yields, further transformation of 0.15 grams brassicasterol 2 to aldehyde 5 would yield approximately 0.09 grams of product.
   Google Scholar
• At this stage of the synthesis, the remaining 13C resonances were unassignable due to the complex spectrum of the steroid mixture.
   Google Scholar