Scripps VIVO scripps research logo

  • Index
  • Log in
  • Home
  • People
  • Organizations
  • Research
  • Events
Search form

Scalable, stereocontrolled total syntheses of (±)-axinellamines A and B

Academic Article
uri icon
  • Overview
  • Identity
  • Additional Document Info
  • View All
scroll to property group menus

Overview

related to degree

  • Rodriguez, Rodrigo, Ph.D. in Chemistry, Scripps Research 2008 - 2014

authors

  • Su, S.
  • Rodriguez, Rodrigo
  • Baran, Phil

publication date

  • 2011

journal

  • Journal of the American Chemical Society  Journal

abstract

  • The development of a simple, efficient, scalable, and stereocontrolled synthesis of a common intermediate en route to the axinellamines, massadines, and palau'amine is reported. This completely new route was utilized to prepare the axinellamines on a gram scale. In a more general sense, three distinct and enabling methodological advances were made during these studies: (1) an ethylene glycol-assisted Pauson-Khand cycloaddition reaction, (2) a Zn/In-mediated Barbier-type reaction, and (3) a TfNH(2)-assisted chlorination-spirocyclization.

subject areas

  • Chemistry Techniques, Synthetic
  • Guanidines
  • Imidazoles
  • Pyrroles
  • Spiro Compounds
  • Stereoisomerism
scroll to property group menus

Identity

PubMed Central ID

  • PMC3164937

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja206191g

PubMed ID

  • 21846138
scroll to property group menus

Additional Document Info

start page

  • 13922

end page

  • 13925

volume

  • 133

issue

  • 35

©2019 The Scripps Research Institute | Terms of Use | Powered by VIVO

  • About
  • Contact Us
  • Support