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Functionalized Phenanthridine and Dibenzopyranone Derivatives through Benzyne Cyclization – Application to the Total Syntheses of Trisphaeridine and N ‐Methylcrinasiadine
Author(s) -
Sanz Roberto,
Fernández Yolanda,
Castroviejo M. Pilar,
Pérez Antonio,
Fañanás Francisco J.
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600621
Subject(s) - aryne , phenanthridine , chemistry , amaryllidaceae alkaloids , total synthesis , stereochemistry , organic chemistry , combinatorial chemistry , alkaloid
A series of regioselectively functionalized benzo[ c ]chromen‐6‐ones, phenanthridinones, and phenanthridine derivatives have been prepared by an anionic cyclization and in situ oxidation sequence starting from 2‐bromobenzyl‐2‐fluorophenyl ethers and amines. These processes involve the generation of a benzyne‐tethered aryllithium intermediate and subsequent 6‐ exo ‐ dig cyclization. By applying this methodology to the appropriate starting materials, short and efficient syntheses of Amaryllidaceae alkaloids trisphaeridine and N ‐methylcrinasiadine have been achieved in good overall yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)