Total Synthesis of Ecteinascidin 743

Key words

ecteinascidin 743 - marine natural product - anti-tumor agent - Strecker amino acid synthesis - Pictet–Spengler reaction - 10-membered lactone

Significance

In 1996, Corey and co-workers reported the first total synthesis of ecteinascidin 743. This rare marine-derived natural product showed potent anti-tumor activities and is now used in the clinic under the name Trabectedin for the treatment of soft tissue sarcoma and ovarian cancer.

Comment

Fragment coupling between A and B was achieved by the Strecker reaction. The piperazine in D is assembled by the Pictet–Spengler reaction. After oxidation of phenol E, the ten-membered lactone is constructed by a one-pot sequence consisting of elimination, deprotection, conjugate addition, and acylation to afford I.

Publication History

Article published online:
25 July 2024