Next Article Table of Contents

An Intramolecular Diels−Alder Strategy for the Asbestinins: Enantioselective Total Syntheses of 11-Acetoxy-4-deoxyasbestinin D and Asbestinin-12

Supporting Info

Michael T. Crimmins* and J. Michael Ellis

Department of Chemistry, Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290

J. Org. Chem., 2008, 73 (5), pp 1649–1660

DOI: 10.1021/jo0712695

Publication Date (Web): October 5, 2007

, *

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

Abstract

The enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12 have been completed. A glycolate aldol reaction provided a diene useful for ring-closing metathesis to form an oxonene, which was ultimately employed as a template to execute a highly stereoselective intramolecular Diels−Alder cycloaddition, forming the hydroisobenzofuran moiety. The absolute configuration of the asbestinin subclass was confirmed via these synthetic efforts.

View: Full Text HTML | Hi-Res PDF | PDF w/ Links

Available Supporting Information for This Article

PDF

jo0712695-file003.pdf (2.3 MB)

Crystallographic Information File

jo0712695-file004.cif (15 KB)

Electronic Supporting Information files are available without a subscription to ACS Web Editions. All files are copyrighted by the American Chemical Society. Files may be downloaded for personal use; users are not permitted to reproduce, republish, redistribute, or resell any Supporting Information, either in whole or in part, in either machine-readable form or any other form. For permission to reproduce this material, contact the ACS Copyright Office by e-mail at copyright@acs.org or by fax at 202-776-8112.

Tools

SciFinder Links

Explore by:

Author of this Article Any Author Research Topic

History

Published In Issue March 07, 2008
Received June 28, 2007

Recommend & Share

Related Content

Total Synthesis of (−)-Spinosyn A: Examination of Structural Features That Govern the Stereoselectivity of the Key Transannular Diels−Alder ReactionThe Journal of Organic Chemistry
- Total Synthesis of (−)-Spinosyn A: Examination of Structural Features That Govern the Stereoselectivity of the Key Transannular Diels−Alder Reaction
  SusAnn M. Winbush, Dustin J. Mergott, and William R. Roush
  The Journal of Organic Chemistry 2008 73 (5), pp 1818–1829
  Abstract: A study of elements of stereochemical control in transannular Diels−Alder reactions leading to the decahydro-as-indacene core of (−)-spinosyn A is described. Initial studies focused on macrocyclic pentaene 9, which includes C(6)-Br and C(8)-OTBS ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Total Synthesis of Brevetoxin AOrganic Letters
- Total Synthesis of Brevetoxin A
  Michael T. Crimmins, J. Lucas Zuccarello, J. Michael Ellis, Patrick J. McDougall, Pamela A. Haile, Jonathan D. Parrish and Kyle A. Emmitte
  Organic Letters 2009 11 (2), pp 489–492
  Abstract: A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner−Wittig olefination. The resulting octacycle was progressed to substrates that ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
An Intramolecular Diels−Alder Approach to the Eunicelins: Enantioselective Total Synthesis of Ophirin BJournal of the American Chemical Society
- An Intramolecular Diels−Alder Approach to the Eunicelins: Enantioselective Total Synthesis of Ophirin B
  Michael T. Crimmins and Brandon H. Brown
  Journal of the American Chemical Society 2004 126 (33), pp 10264–10266
  Abstract: The enantioselective synthesis of the eunicellin ophirin B has been completed. A ring-closing metathesis provides efficient access to the oxonene ring, and a highly diastereoselective intramolecular Diels−Alder reaction results in the formation of the ...
  Abstract | Full Text HTML | Hi-Res PDF

Featured Article

An Intramolecular Diels−Alder Strategy for the Asbestinins: Enantioselective Total Syntheses of 11-Acetoxy-4-deoxyasbestinin D and Asbestinin-12

Abstract

Available Supporting Information for This Article

PDF

Crystallographic Information File

Tools

SciFinder Links

History

Recommend & Share

Related Content

Total Synthesis of (−)-Spinosyn A: Examination of Structural Features That Govern the Stereoselectivity of the Key Transannular Diels−Alder Reaction

Total Synthesis of Brevetoxin A

An Intramolecular Diels−Alder Approach to the Eunicelins: Enantioselective Total Synthesis of Ophirin B

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES