A route to the 9,10-secosteroid astrogorgiadiol featuring a key sp(2)-sp(3) Suzuki type cross-coupling

作者：Medard Guillaume^*

来源：Tetrahedron, 2014, 70(2): 186-196.

DOI：10.1016/j.tet.2013.11.102

• Secosteroid
• Astrogorgiadiol
• Calicoferol
• Astrogorgol
• Grundmann ketone
• Cross-coupling

The described semi-synthetic route differs from the previously published approaches by an original C-7-C-8 disconnection. The kinetic enol triflate of Grundmann ketone was chosen as the CD-ring platform on which to couple an A-ring synthon via a challenging sp(2)-sp(3) cross-coupling. A range of A-ring synthons was synthesized to allow the investigations of various conditions of metal-catalyzed couplings. Suzuki-type chemistry provided a useful (89% yield) answer. Whereas the last step of the designed route a regioselective opening of the epoxide obtained from the alkene, product of the coupling reaction proved more challenging than expected, a hydroboration endgame route completed a formal synthesis of (-)-astrogorgiadiol.

• 出版日期2014-1-14