related to degree

• Newhouse, Timothy, Ph.D. in Chemistry, Scripps Research 2006 - 2010

authors

• Newhouse, Timothy
• Baran, Phil

publication date

• 2008

journal

• Journal of the American Chemical Society  Journal

abstract

• new process for the union of anilines with tryptamine derivatives has been developed, furnishing C-3 quaternized pyrroloindoline architectures. This chemoselective coupling of a tryptamine with 1.2 equiv of 2-iodoaniline proceeds efficiently on a gram-scale using only the simple reagents N-iodosuccinimide and triethylamine. Using this new reaction, the complex natural product psychotrimine has been fashioned with a rare level of efficiency and practicality. From a readily available bromotryptamine, only four steps (41-45% overall isolated yield) are necessary to procure gram quantities of the natural product. Functional group manipulations, protecting group chemistry, and unnecessary redox fluctuations have been minimized.

subject areas

• Indole Alkaloids
• Molecular Structure
• Stereoisomerism

International Standard Serial Number (ISSN)

• 0002-7863

Digital Object Identifier (DOI)

• 10.1021/ja8042307

PubMed ID

• 18656919

start page

• 10886

end page

• 10887

volume

• 130

issue

• 33