Dienyne ring-closing metathesis approach for the construction of taxosteroids.
A cascade dienyne ring-closing metathesis approach has been applied to the synthesis of the tetracyclic carbon framework of a new class of hybrid compounds-the taxosteroids-possessing carbon frameworks incorporating moieties characteristic of both taxanes (such as AB rings) and steroids (i.e., CD system and side chain). This tandem cyclization is highly stereoselective, allowing the one-step formation of the bicyclo[5.3.1]undecene system characteristic of taxol. In this work we describe the scope and limitations of such cyclizations.
Aldegunde
María J
MJ
Departamento de Química Orgánica e Unidade Asociada ó C.S.I.C. Facultade de Química, Universidade de Santiago, 15782 Santiago de Compostela, Spain.
García-Fandiño
Rebeca
R
Castedo
Luis
L
Granja
Juan R
JR
D000466:Alkadienes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D003500:Cyclization; D008956:Models, Chemical; D015394:Molecular Structure; D017239:Paclitaxel / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000737:chemistry; D013256:Steroids / Q000138:chemical synthesis*; D043823:Taxoids / Q000138:chemical synthesis*
D000466:Alkadienes; D000480:Alkynes; D001643:Bridged Bicyclo Compounds; D011083:Polycyclic Compounds; D013256:Steroids; D043823:Taxoids; D002244:Carbon; D017239:Paclitaxel