Synthetic study toward ecteinascidin 743: concise construction of the diazabicyclo[3.3.1]nonane skeleton and assembly of the pentacyclic core

Taro Enomoto; Yoshizumi Yasui; Yoshiji Takemoto

doi:10.1021/jo100788j

Synthetic study toward ecteinascidin 743: concise construction of the diazabicyclo[3.3.1]nonane skeleton and assembly of the pentacyclic core

J Org Chem. 2010 Jul 16;75(14):4876-9. doi: 10.1021/jo100788j.

Authors

Taro Enomoto¹, Yoshizumi Yasui, Yoshiji Takemoto

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan. [email protected]

PMID: 20557114
DOI: 10.1021/jo100788j

Abstract

Synthesis of the pentacyclic core of ecteinascidin 743 is described. This synthesis features concise construction of the diazabicyclo[3.3.1]nonane skeleton using gold(I)-catalyzed one-pot keto amide formation, acid-promoted enamide formation, and oxidative Friedel-Crafts cyclization as the key steps.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biological Products / chemistry*
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / chemistry
Catalysis
Cyclization
Molecular Structure
Oxidation-Reduction
Phenylalanine / chemical synthesis*
Phenylalanine / chemistry
Polycyclic Aromatic Hydrocarbons / chemistry*
Stereoisomerism
Tetrahydroisoquinolines / chemistry*

Substances

Biological Products
Bridged Bicyclo Compounds, Heterocyclic
Polycyclic Aromatic Hydrocarbons
Tetrahydroisoquinolines
Phenylalanine