Synthesis of the Pluramycins 2: Total Synthesis and Structure Assignment of Saptomycin B
Publication type: Journal Article
Publication date: 2013-12-16
General Medicine
Abstract
A concise, highly convergent total synthesis of saptomycin B, a member of the pluramycin class of antitumor antibiotics, is reported. The target compound was assembled from four building blocks (a tricyclic platform, two sugars, and an alkynal) in 15% yield through 10 synthetic operations. The key steps included the regioselective installation of two amino sugars (L-vancosamine and D-angolosamine) on the tricycle and the efficient construction of the tetracyclic skeleton by an aldol reaction followed by formation of the pyranone. The unknown configuration at C14 was assigned as R.
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Citations from 2024:
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KITAMURA K. et al. Synthesis of the Pluramycins 2: Total Synthesis and Structure Assignment of Saptomycin B // Angewandte Chemie. 2013. Vol. 126. No. 5. pp. 1286-1289.
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KITAMURA K., MAEZAWA Y., Ando Y., Kusumi T., MATSUMOTO T., Suzuki K. Synthesis of the Pluramycins 2: Total Synthesis and Structure Assignment of Saptomycin B // Angewandte Chemie. 2013. Vol. 126. No. 5. pp. 1286-1289.
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TY - JOUR
DO - 10.1002/ange.201308017
UR - https://doi.org/10.1002/ange.201308017
TI - Synthesis of the Pluramycins 2: Total Synthesis and Structure Assignment of Saptomycin B
T2 - Angewandte Chemie
AU - KITAMURA, Kei
AU - MAEZAWA, Yoshihiko
AU - Ando, Yoshio
AU - Kusumi, Takenori
AU - MATSUMOTO, TAKASHI
AU - Suzuki, Keisuke
PY - 2013
DA - 2013/12/16
PB - Wiley
SP - 1286-1289
IS - 5
VL - 126
SN - 0044-8249
SN - 1521-3757
ER -
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@article{2013_KITAMURA,
author = {Kei KITAMURA and Yoshihiko MAEZAWA and Yoshio Ando and Takenori Kusumi and TAKASHI MATSUMOTO and Keisuke Suzuki},
title = {Synthesis of the Pluramycins 2: Total Synthesis and Structure Assignment of Saptomycin B},
journal = {Angewandte Chemie},
year = {2013},
volume = {126},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002/ange.201308017},
number = {5},
pages = {1286--1289},
doi = {10.1002/ange.201308017}
}
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MLA
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KITAMURA, Kei, et al. “Synthesis of the Pluramycins 2: Total Synthesis and Structure Assignment of Saptomycin B.” Angewandte Chemie, vol. 126, no. 5, Dec. 2013, pp. 1286-1289. https://doi.org/10.1002/ange.201308017.