An Efficient Synthesis of 3-Hetero-13,14-dihydro Prostaglandin F1α Analogues
- 15 February 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (5) , 791-794
- https://doi.org/10.1021/ol015613a
Abstract
[structure: see text]. A new class of 3-hetero-13,14-dihydro prostaglandin F(1)(alpha) analogues was synthesized from a common intermediate. The latter was constructed via a two-step, three-component process. The lower chain, containing the 15-(phenoxymethyl) group, was synthesized in enantiopure form using Jacobsen's (salen)Co-catalyzed kinetic resolution of a terminal epoxide with phenol.Keywords
This publication has 8 references indexed in Scilit:
- Asymmetric Catalytic Synthesis of α-Aryloxy Alcohols: Kinetic Resolution of Terminal Epoxides via Highly Enantioselective Ring-Opening with PhenolsJournal of the American Chemical Society, 1999
- Selective deprotection of trialkylsilyl ethers using fluorosilicic acidThe Journal of Organic Chemistry, 1992
- Clean and convenient procedure for converting primary alkyl iodides and .alpha.,.omega.-diiodoalkanes into the corresponding alkyllithium derivatives by treatment with tert-butyllithiumThe Journal of Organic Chemistry, 1990
- Convenient general method for the preparation of primary alkyllithiums by lithium-iodine exchangeThe Journal of Organic Chemistry, 1990
- 2-thienyl(cyano)copper lithium. A lower order,Tetrahedron Letters, 1987
- Rapid removal of protecting groups from peptides by catalytic transfer hydrogenation with 1,4-cyclohexadieneThe Journal of Organic Chemistry, 1978
- Total synthesis of prostaglandins. II. Prostaglandin E1Journal of the American Chemical Society, 1972
- Stereo-controlled synthesis of dl-prostaglandins F2.alpha. and E2Journal of the American Chemical Society, 1969