An efficient synthesis of 3-hetero-13,14-dihydro prostaglandin F1alpha analogues.
[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.
Gu
J
J
Department of Chemistry, Wayne State University, Detroit, Michigan 48202-3489, USA.
Dirr
M J
MJ
Wang
Y
Y
Soper
D L
DL
De
B
B
Wos
J A
JA
Johnson
C R
CR
D000818:Animals; D019556:COS Cells; D005998:Glycine / Q000737:chemistry; D007202:Indicators and Reagents; D011460:Prostaglandins F / Q000138:chemical synthesis* / Q000378:metabolism; D011461:Prostaglandins F, Synthetic / Q000138:chemical synthesis* / Q000378:metabolism; D011982:Receptors, Prostaglandin / Q000378:metabolism; D013237:Stereoisomerism
D007202:Indicators and Reagents; D011460:Prostaglandins F; D011461:Prostaglandins F, Synthetic; D011982:Receptors, Prostaglandin; D005998:Glycine; C100006:prostaglandin F1