Corey EJ,
*,
Gin DY,
Kania RS.
Harvard University, Cambridge, USA
Enantioselective Total Synthesis of Ecteinascidin 743.
J. Am. Chem. Soc. 1996;
118: 9202-9203
DOI:
10.1021/ja962480t
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.
