Prostaglandin E2 methyl ester

Chen, S. Janda, K. D. Synthesis of Prostaglandin E2 Methyl Ester on a Soluble-Polymer Support for the Construction of Prostanoid Libraries, J. Am. Chem. Soc. 1997, 119, 8724. 

To obtain the open-chain prostaglandin E2 methyl ester (31), the symmetrical Cio alkyne 30 was employed as the source of the C5 unit to be introduced into the starting material 29 (Scheme 7). The yield of this less symmetrical alkyne metathesis was 51% [27]. The macro-... 

Chen S, Janda KD, Synthesis of prostaglandin E2 methyl ester on a soluble-polymer support for the construction of prostanoid libraries, J. Am. Chem. Soc., 119 8724-8725, 1997. 

TrimethylsUyl Group Transfer. The major use of this reagent has been in the protection of functional groups (particularly hydroxyl) as the trimethylsUyl derivatives. This is illustrated in work on brefeldin A (eq 1) and in the S3mthesis of prostaglandin E2 methyl ester (eq 2), where selective protection of two hydroxyl groups occurred. In addition, axial alcohols are converted into trimethylsilyl ethers much faster than equatorial alcohols. Another multifunctional molecule which has been protected is the alcohol produced by cleaving the enone shown in eq 3. ... 

Schneider, C., Manier, M.L., Hachey, D.L., and Brash. A.R. (2002) Detection of the 15-acetate of prostaglandin E2 methyl ester as a prominent component of the prostaglandins in the gorgonian coral Plexaura homomalla. Lipids, 37, 217-221. 

Stabilization of prostaglandins in the solid state by CDs and their derivatives has also been reported. The stability of 16,1 6-dimethyl-/ra .v-A2-prostaglandin Ei methyl ester against dehydration and isomerization in the solid state is increased by complex formation with P-CD.529 As shown in Fig. 126, the stability of prostaglandin E2 is decreased by the... 

FIGURE 11.12 Prostaglandins E2 and Fj combinatorial libraries. (From Chen, S. and Janda, K.D., Synthesis of prostaglandin Ej methyl ester on a soluble-polymer support for the construction of prostanoid libraries, J. Am. Chem. Soc., 119, 8724, 1995 Chen, S. and Janda, K.D., Total synthesis of naturally occurring prostaglandin F2on a non-cross-linked polystyrene support. Tetrahedron Lett., 39, 3943, 1998.)... 

---