Biomaterial Database

Synthesis of macrolide prostaglandin analogs. 1981

N H Andersen, and S Imamoto, and N Subramanian

Prostaglandin analogs of the E- and F2 alpha-functional type, which are constrained to conformations in which the side-chains are close in space and specifically aligned in the terminal portions by covalent bonding, have been synthesized. These analogs are 1, (omega-1)-macrolides. The syntheses proceeded from aldehyde intermediate I via the Emmon's condensation with dimethyl n-(dimethyl-t-butylsilyloxy)2-oxoalkylphosphonate anions (II a or b). The macrolide closures were performed using 2, 2'-dipyridyl disulfide. For the synthesis of 9-ketoprostaglandin macrolides, a free 9-hydroxy is available for oxidation after macrolide closure, so long as the 9-position is protected as the acetate rather than benzoate. Chiroptical data revealed that the conformations of the macrolide prostaglandins are unchanged (relative to the natural unconstrained prostaglandins) in the vicinity of the five-membered ring and the allyl alcohol unit by the formation of the macrolide linkage.

UI	MeSH Term	Description	Entries
D008722	Methods	A series of steps taken in order to conduct research.	Techniques,Methodological Studies,Methodological Study,Procedures,Studies, Methodological,Study, Methodological,Method,Procedure,Technique
D011458	Prostaglandins E	(11 alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-oic acid (PGE(1)); (5Z,11 alpha,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid (PGE(2)); and (5Z,11 alpha,13E,15S,17Z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-oic acid (PGE(3)). Three of the six naturally occurring prostaglandins. They are considered primary in that no one is derived from another in living organisms. Originally isolated from sheep seminal fluid and vesicles, they are found in many organs and tissues and play a major role in mediating various physiological activities.	PGE
D011461	Prostaglandins F, Synthetic	Analogs or derivatives of prostaglandins F that do not occur naturally in the body. They do not include the product of the chemical synthesis of hormonal PGF.	PGF Synthetic,Prostaglandin F Analogs,Prostaglandin F Analogues,Synthetic Prostaglandins F,Analogs, Prostaglandin F,Analogues, Prostaglandin F,Synthetic, PGF
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer