Highly diastereoselective total synthesis of the anti-tumoral agent (±)-Spisulosine (ES285) from a Morita-Baylis-Hillman adduct

We disclose herein a new approach for the highly diastereoselective total synthesis of the anti-tumoral agent (+/-)-Spisulosine. The synthesis was accomplished in seven steps with an overall yield of 10%. The key step involves the transformation of a Morita-Baylis-Hillman into an acyloin, which was subsequently used as substrate in a highly diastereoselective reductive amination reaction. (C) 2010 Elsevier Ltd. All rights reserved.