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Title: Total synthesis of gracilioether F. Development and application of Lewis acid promoted ketene–alkene [2+2] cycloadditions and late-stage C—H oxidation

Abstract

The first synthesis of gracilioether F, a polyketide natural product with an unusual tricyclic core and five contiguous stereocenters, is described. Key steps of the synthesis include a Lewis acid promoted ketene–alkene [2+2] cycloaddition and a late-stage carboxylic acid directed C(sp³)—H oxidation. The synthesis requires only eight steps from norbornadiene.

Authors:
 [1];  [1]
  1. Indiana Univ., Bloomington, IN (United States)
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1171255
Resource Type:
Journal Article
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Volume: 53; Journal Issue: 52; Journal ID: ISSN 1433-7851
Publisher:
Wiley
Country of Publication:
United States
Language:
ENGLISH
Subject:
C—H oxidation; cycloaddition; gracilioether F; ketenes; total synthesis

Citation Formats

Rasik, Christopher M., and Brown, M. Kevin. Total synthesis of gracilioether F. Development and application of Lewis acid promoted ketene–alkene [2+2] cycloadditions and late-stage C—H oxidation. United States: N. p., 2014. Web. doi:10.1002/anie.201408055.
Rasik, Christopher M., & Brown, M. Kevin. Total synthesis of gracilioether F. Development and application of Lewis acid promoted ketene–alkene [2+2] cycloadditions and late-stage C—H oxidation. United States. https://doi.org/10.1002/anie.201408055
Rasik, Christopher M., and Brown, M. Kevin. 2014. "Total synthesis of gracilioether F. Development and application of Lewis acid promoted ketene–alkene [2+2] cycloadditions and late-stage C—H oxidation". United States. https://doi.org/10.1002/anie.201408055.
@article{osti_1171255,
title = {Total synthesis of gracilioether F. Development and application of Lewis acid promoted ketene–alkene [2+2] cycloadditions and late-stage C—H oxidation},
author = {Rasik, Christopher M. and Brown, M. Kevin},
abstractNote = {The first synthesis of gracilioether F, a polyketide natural product with an unusual tricyclic core and five contiguous stereocenters, is described. Key steps of the synthesis include a Lewis acid promoted ketene–alkene [2+2] cycloaddition and a late-stage carboxylic acid directed C(sp³)—H oxidation. The synthesis requires only eight steps from norbornadiene.},
doi = {10.1002/anie.201408055},
url = {https://www.osti.gov/biblio/1171255}, journal = {Angewandte Chemie (International Edition)},
issn = {1433-7851},
number = 52,
volume = 53,
place = {United States},
year = {Mon Dec 22 00:00:00 EST 2014},
month = {Mon Dec 22 00:00:00 EST 2014}
}