First total synthesis and stereochemical revision of okaramine M

We describe the first total synthesis of the reported and revised structures of okaramine M ( 1 and 7) through the Ugi three-component reaction of pyrroloindole imine 10 with p-methoxyphenyl isonitrile and N-Boc- l-tryptophan, followed by cyclization and epimerization.

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2010-11, Vol.51 (46), p.6003-6005
Main Authors: Iizuka, Toshimasa, Takiguchi, Satoshi, Kumakura, Yuh-suke, Tsukioka, Naoki, Higuchi, Kazuhiro, Kawasaki, Tomomi
Format: Article
Language:English
Subjects:
Asymmetric synthesis
Diketopiperazine
Imines
Oxidation
Pyrrolo[2,3- b]indole
Synthesis (chemistry)
Tetrahedrons
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We describe the first total synthesis of the reported and revised structures of okaramine M ( 1 and 7) through the Ugi three-component reaction of pyrroloindole imine 10 with p-methoxyphenyl isonitrile and N-Boc- l-tryptophan, followed by cyclization and epimerization.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.09.026