Chapter 16. Prostaglandins and Related Compounds
作者： Jehan F. Bagli
DOI: 10.1016/S0065-7743(08)60339-5
关键词: Intramolecular force 、 Lactone 、 Cyclopentane 、 Stereoselectivity 、 Ketone 、 Cyclopentadienyl complex 、 Aldol condensation 、 Organic chemistry 、 Cyclopentanol 、 Chemistry
摘要: Publisher Summary This chapter elaborates chemical advances in prostaglandins (PG). Nasal decongestion, lowering blood pressure, treating gastric ulcers, infertile semen, inducing labor, and thrombosis are some of the promising therapeutic areas that being investigated for prostaglandins. The syntheses PGE1 PGE2 their racemic its optically active presented. Their synthetic sequences particularly characterized by mild specific reaction conditions. first two from this group involved an intramolecular aldol condensation to generate desired cyclopentanol, followed transformation amino at C-9 a ketone function. penta substituted cyclopentane was synthesized six step stereoselective sequence starting with cyclopentadienyl sodium. Lactone transformed five steps α,β-unsaturated ketone. converted more PGF2. A also developed whereby C-11 C-15 alcohols can be protected as tetrahydropyranyl (THP) ethers generated oxidation leading PGE2.
sci-hub.se 参考文章(26)
YASUO YURA, JUNYA IDE, A Total Synthesis of a dl-Prostaglandin B1 Chemical & Pharmaceutical Bulletin. ,vol. 17, pp. 408- 410 ,(1969) , 10.1248/CPB.17.408
E W Horton, Hypotheses on physiological roles of prostaglandins. Physiological Reviews. ,vol. 49, pp. 122- 161 ,(1969) , 10.1152/PHYSREV.1969.49.1.122
Masateru Miyano, Synthetic studies on prostaglandins II Tetrahedron Letters. ,vol. 10, pp. 2771- 2774 ,(1969) , 10.1016/S0040-4039(01)88265-4
Udo Axen, Frank H. Lincoln, John E. Pike, John L. Thompson, William Paul Schneider, The synthesis of prostaglandin E1 and related substances. Journal of the American Chemical Society. ,vol. 91, pp. 5372- 5378 ,(1969) , 10.1021/JA01047A029
Masateru Miyano, C.R. Dorn, Total synthesis of 15-dehydro-prostaglandin E1. Tetrahedron Letters. ,vol. 10, pp. 1615- 1618 ,(1969) , 10.1016/S0040-4039(01)87960-0
Elias J. Corey, Isidoros Vlattas, Kenn Harding, Total synthesis of natural (levo) and enantiomeric (dextro) forms of prostaglandin El. Journal of the American Chemical Society. ,vol. 91, pp. 535- 536 ,(1969) , 10.1021/JA01030A077
Susan Heim Ford, Josef Fried, Smooth muscle activity of rac.-7-oxaprostaglandin F1α and related substances Life Sciences. ,vol. 8, pp. 983- 987 ,(1969) , 10.1016/0024-3205(69)90430-5
Robert B. Morin, Douglas O. Spry, Kenneth L. Hauser, Richard A. Mueller, Approaches to the chemical synthesis of the prostaglandins Tetrahedron Letters. ,vol. 9, pp. 6023- 6028 ,(1968) , 10.1016/S0040-4039(00)70783-0
JOSEF FRIED, T. S. SANTHANAKRISHNAN, J. HIMIZU, C. H. LIN, SUSAN HEIM FORD, B. RUBIN, E. O. GRIGAS, Prostaglandin Antagonists: Synthesis and Smooth Muscle Activity Nature. ,vol. 223, pp. 208- 210 ,(1969) , 10.1038/223208A0
Elias J. Corey, Ned M. Weinshenker, Thomas K. Schaaf, Willy Huber, Stereo-controlled synthesis of dl-prostaglandins F2.alpha. and E2 Journal of the American Chemical Society. ,vol. 91, pp. 5675- 5677 ,(1969) , 10.1021/JA01048A062