Synthetic studies of the 18-membered antitumor macrolide, tedanolide. 3. Stereocontrolled synthesis of the C1-C12 part via a synthesis of the C1-C7 fragment by a mismatched but efficient sharpless dihydroxylation and its coupling with the C8-C11 fragment.
Publication type: Journal Article
Publication date: 2011-12-08
scimago Q3
wos Q3
SJR: 0.349
CiteScore: 2.7
Impact factor: 1.3
ISSN: 00092363, 13475223
PubMed ID:
10212381
General Chemistry
Drug Discovery
General Medicine
Abstract
The C1-C12 part (4) of tedanolide (1) was synthesized starting from methyl (R)-3-hydroxy-2-methylpropionate (11a) via a coupling between the C1-C7 aldehyde (6) and the C8-C11 iodoalkene (7a). For a synthesis of 6, a mismatched but highly efficient Sharpless dihydroxylation of the alpha, beta-unsaturated ester (15) with AD-mix-alpha was successfully applied. Compound 7a was synthesized using hydrozirconation to the alkyne (32).
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Matsushima T. et al. Synthetic studies of the 18-membered antitumor macrolide, tedanolide. 3. Stereocontrolled synthesis of the C1-C12 part via a synthesis of the C1-C7 fragment by a mismatched but efficient sharpless dihydroxylation and its coupling with the C8-C11 fragment. // Chemical and Pharmaceutical Bulletin. 2011. Vol. 47. No. 3. pp. 308-321.
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Matsushima T. Synthetic studies of the 18-membered antitumor macrolide, tedanolide. 3. Stereocontrolled synthesis of the C1-C12 part via a synthesis of the C1-C7 fragment by a mismatched but efficient sharpless dihydroxylation and its coupling with the C8-C11 fragment. // Chemical and Pharmaceutical Bulletin. 2011. Vol. 47. No. 3. pp. 308-321.
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TY - JOUR
DO - 10.1248/cpb.47.308
UR - https://doi.org/10.1248/cpb.47.308
TI - Synthetic studies of the 18-membered antitumor macrolide, tedanolide. 3. Stereocontrolled synthesis of the C1-C12 part via a synthesis of the C1-C7 fragment by a mismatched but efficient sharpless dihydroxylation and its coupling with the C8-C11 fragment.
T2 - Chemical and Pharmaceutical Bulletin
AU - Matsushima, Tomohiro
PY - 2011
DA - 2011/12/08
PB - Pharmaceutical Society of Japan
SP - 308-321
IS - 3
VL - 47
PMID - 10212381
SN - 0009-2363
SN - 1347-5223
ER -
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@article{2011_Matsushima,
author = {Tomohiro Matsushima},
title = {Synthetic studies of the 18-membered antitumor macrolide, tedanolide. 3. Stereocontrolled synthesis of the C1-C12 part via a synthesis of the C1-C7 fragment by a mismatched but efficient sharpless dihydroxylation and its coupling with the C8-C11 fragment.},
journal = {Chemical and Pharmaceutical Bulletin},
year = {2011},
volume = {47},
publisher = {Pharmaceutical Society of Japan},
month = {dec},
url = {https://doi.org/10.1248/cpb.47.308},
number = {3},
pages = {308--321},
doi = {10.1248/cpb.47.308}
}
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Matsushima, Tomohiro, et al. “Synthetic studies of the 18-membered antitumor macrolide, tedanolide. 3. Stereocontrolled synthesis of the C1-C12 part via a synthesis of the C1-C7 fragment by a mismatched but efficient sharpless dihydroxylation and its coupling with the C8-C11 fragment..” Chemical and Pharmaceutical Bulletin, vol. 47, no. 3, Dec. 2011, pp. 308-321. https://doi.org/10.1248/cpb.47.308.