New strategies for the synthesis of biologically important tetrapyrroles. The "B,C + D + A" approach to linear tetrapyrroles.
Linear tetrapyrroles related to phytochrome (1) were prepared in enantiospecific fashion by a new strategy beginning with ring-B,C synthons of type 19 (bis-iododipyrrins). Rings A and D were elaborated by Pd(0)-mediated coupling of 19a with the appropriate alkyne acid or amide derivatives 9 and 20, followed by intramolecular cyclization (method C: BC + D + A --> ABCD).
Jacobi
P A
PA
Hall-Atwater Laboratories, Wesleyan University, Middletown, Connecticut 06459-0180, USA.
Coutts
L D
LD
Guo
J
J
Hauck
S I
SI
Leung
S H
SH
D009682:Magnetic Resonance Spectroscopy; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D045725:Tetrapyrroles
D011758:Pyrroles; D045725:Tetrapyrroles