Total Synthesis of (−)-8-O-Methyltetrangomycin (MM 47755)
Publication type: Journal Article
Publication date: 2006-05-16
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
16737300
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A stereoselective total synthesis of the natural antibiotic (-)-8-O-methyltetrangomycin 1 is reported. The essential steps for this convergent synthesis are the transformation of a geraniol epoxide into a chiral octadiyne derivative, which was converted into a triyne. The cobalt-mediated [2+2+2] cycloaddition of the triyne led to a benz[a]anthracene system, which was oxidized with Ag(Py)(2)MnO(4) to a benz[a]anthraquinone. Deprotection with aqueous HF in acetonitrile and photooxidation afforded the desired product (-)-1. [reaction: see text]
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Total citations:
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Citations from 2024:
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(7.69%)
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MLA
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GOST
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Kesenheimer C., Groth U. Total Synthesis of (−)-8-O-Methyltetrangomycin (MM 47755) // Organic Letters. 2006. Vol. 8. No. 12. pp. 2507-2510.
GOST all authors (up to 50)
Copy
Kesenheimer C., Groth U. Total Synthesis of (−)-8-O-Methyltetrangomycin (MM 47755) // Organic Letters. 2006. Vol. 8. No. 12. pp. 2507-2510.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ol060667b
UR - https://doi.org/10.1021/ol060667b
TI - Total Synthesis of (−)-8-O-Methyltetrangomycin (MM 47755)
T2 - Organic Letters
AU - Kesenheimer, Christian
AU - Groth, Ulrich
PY - 2006
DA - 2006/05/16
PB - American Chemical Society (ACS)
SP - 2507-2510
IS - 12
VL - 8
PMID - 16737300
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2006_Kesenheimer,
author = {Christian Kesenheimer and Ulrich Groth},
title = {Total Synthesis of (−)-8-O-Methyltetrangomycin (MM 47755)},
journal = {Organic Letters},
year = {2006},
volume = {8},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/ol060667b},
number = {12},
pages = {2507--2510},
doi = {10.1021/ol060667b}
}
Cite this
MLA
Copy
Kesenheimer, Christian, and Ulrich Groth. “Total Synthesis of (−)-8-O-Methyltetrangomycin (MM 47755).” Organic Letters, vol. 8, no. 12, May. 2006, pp. 2507-2510. https://doi.org/10.1021/ol060667b.