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Synthesis of lepadiformine using a hydroamination transform

Academic Article
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Overview

related to degree

  • Tabor, Greg Martin, Ph.D. in Organic Chemistry, Scripps Research 2010 - 2016

authors

  • Tabor, Greg Martin
  • Shenvi, Ryan

publication date

  • December 2015

journal

  • Organic Letters  Journal

abstract

  • Dissection of lepadiformine by a double hydroamination transform affords a simple achiral amino diene. This reaction is accomplished in the forward sense by amine-directed hydroboration and an oxidative alkyl shift to nitrogen, both of which occur with high stereoselectivity to generate three stereogenic centers and the lepadiformine skeleton.

subject areas

  • Alkaloids
  • Amines
  • Animals
  • Cyclization
  • Molecular Structure
  • Stereoisomerism
  • Urochordata
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/acs.orglett.5b02992

PubMed ID

  • 26584132
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Additional Document Info

start page

  • 5776

end page

  • 5779

volume

  • 17

issue

  • 23

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