Prev. Article Next Article Table of Contents

Letter

Silylative Dieckmann-Like Cyclizations of Ester-Imides (and Diesters)

Supporting Info

Thomas R. Hoye,* Vadims Dvornikovs, and Elena Sizova

Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455

Org. Lett., 2006, 8 (23), pp 5191–5194

DOI: 10.1021/ol061988q

Publication Date (Web): October 11, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, hoye@chem.umn.edu

Abstract

Trialkylsilyl triflates effect cyclization of ester-imides such as 2 to produce adducts such as 4a. Trapping of the in situ generated, nucleophilic ketene acetal (cf. 5a) is a key aspect of the transformation. A range of substrates amenable to this operationally simple reaction is reported. In many instances the levels of diastereoselectivity are very high. Mechanistic points are inferred from spectroscopic observations.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue November 09, 2006
Received August 10, 2006

Recommend & Share

Related Content

Enantiospecific Total Syntheses of Kapakahines B and FJournal of the American Chemical Society
- Enantiospecific Total Syntheses of Kapakahines B and F
  Timothy Newhouse, Chad A. Lewis and Phil S. Baran
  Journal of the American Chemical Society 2009 131 (18), pp 6360–6361
  Abstract: Gram-scale, enantiospecific total syntheses of the anti-leukemia marine natural products kapakahines B and F have been completed. Two powerfully simplifying transformations have enabled the gram-scale synthesis of this natural product family: (1) an ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Total Synthesis of (−)-AcutumineJournal of the American Chemical Society
- Total Synthesis of (−)-Acutumine
  Fang Li, Samuel S. Tartakoff and Steven L. Castle
  Journal of the American Chemical Society 2009 131 (19), pp 6674–6675
  Abstract: The first total synthesis of the tetracyclic alkaloid (−)-acutumine is described. Key reactions include an asymmetric ketone allylation mediated by Nakamura’s chiral allylzinc reagent, an anionic oxy-Cope rearrangement, and the Lewis acid-promoted ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Total Synthesis of UCS1025AJournal of the American Chemical Society
- Total Synthesis of UCS1025A
  Tristan H. Lambert and Samuel J. Danishefsky
  Journal of the American Chemical Society 2006 128 (2), pp 426–427
  Abstract: The enantioselective total synthesis of the telomerase inhibitor UCS1025A has been accomplished. The key transformation involves a remarkable boron Reformatsky coupling of iodolactone 13 and aldehyde 17.
  Abstract | Full Text HTML | Hi-Res PDF

Letter

Silylative Dieckmann-Like Cyclizations of Ester-Imides (and Diesters)

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Enantiospecific Total Syntheses of Kapakahines B and F

Total Synthesis of (−)-Acutumine

Total Synthesis of UCS1025A

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES