Synthesis of natural ecteinascidins (ET-729, ET-745, ET-759B, ET-736, ET-637, ET-594) from cyanosafracin B.
The semisynthetic process initially described for the synthesis of 1 (ET-743) has been extended to the preparation of other natural ecteinascidins. For the synthesis of 2 (ET-729) a demethylation of a N-Me intermediate was carried out by a selective oxidation with MCPBA. Other natural ecteinascidins (ET-745, ET-759B, ET-736, ET-637, ET-594) were accessible from key intermediate 25. The described methodologies allow for the preparation of a wide variety of ecteinascidins by procedures that can be easily scaled up.
Menchaca
Roberto
R
Pharma Mar, S. A. C/Avda de los Reyes, 1.P.I. La Mina-Norte. 28770 Colmenar Viejo, Madrid, Spain.
Martínez
Valentín
V
Rodríguez
Alberto
A
Rodríguez
Natividad
N
Flores
María
M
Gallego
Pilar
P
Manzanares
Ignacio
I
Cuevas
Carmen
C
D001392:Azocines / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011809:Quinones / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013057:Spectrum Analysis
D001392:Azocines; D007546:Isoquinolines; D011809:Quinones; C413208:cyanosafracin B