Total Synthesis and Structural Revision of Cephalosporolide J
Publication type: Journal Article
Publication date: 2022-10-24
scimago Q3
wos Q3
SJR: 0.437
CiteScore: 3.3
Impact factor: 1.4
ISSN: 09365214, 14372096
Organic Chemistry
Abstract
Herein, we report the first total synthesis of cephalosporolide J, which is a deep sea sediment derived polyketide harboring a unique bicyclo[3.3.0]furanolactone moiety. The adopted synthetic strategy consisted of the alkynylation of γ-lactone with lithium alkynyltrifluoroborate followed by a spiroketalization triggered by hydrogenation of the triple bond. Through this synthesis, the correct structure of cephalosporolide J is shown to be that of the 9-epi stereoisomer of the structure originally proposed.
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Ota K., Miyaoka H. Total Synthesis and Structural Revision of Cephalosporolide J // Synlett. 2022. Vol. 34. No. 03. pp. 271-276.
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Ota K., Miyaoka H. Total Synthesis and Structural Revision of Cephalosporolide J // Synlett. 2022. Vol. 34. No. 03. pp. 271-276.
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TY - JOUR
DO - 10.1055/a-1967-1284
UR - https://doi.org/10.1055/a-1967-1284
TI - Total Synthesis and Structural Revision of Cephalosporolide J
T2 - Synlett
AU - Ota, Koichiro
AU - Miyaoka, Hiroaki
PY - 2022
DA - 2022/10/24
PB - Georg Thieme Verlag KG
SP - 271-276
IS - 03
VL - 34
SN - 0936-5214
SN - 1437-2096
ER -
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BibTex (up to 50 authors)
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@article{2022_Ota,
author = {Koichiro Ota and Hiroaki Miyaoka},
title = {Total Synthesis and Structural Revision of Cephalosporolide J},
journal = {Synlett},
year = {2022},
volume = {34},
publisher = {Georg Thieme Verlag KG},
month = {oct},
url = {https://doi.org/10.1055/a-1967-1284},
number = {03},
pages = {271--276},
doi = {10.1055/a-1967-1284}
}
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MLA
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Ota, Koichiro, and Hiroaki Miyaoka. “Total Synthesis and Structural Revision of Cephalosporolide J.” Synlett, vol. 34, no. 03, Oct. 2022, pp. 271-276. https://doi.org/10.1055/a-1967-1284.