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Total Synthesis of Acaulide and Acaulone A.
Org Lett. 2020 Jul 17; 22(14):5545-5549.OL

Abstract

Acaulide and acaulone A, which contain 14-membered macrodiolides, were isolated from a culture of Acaulium sp. H-JQSF. The antiosteoporosis activity of acaulide is expected to contribute to drug discovery research for an aging society. We herein report the first total synthesis of acaulide, acaulone A, and 10-keto-acaudiol A. Acaulide and acaulone A were synthesized via the late stage Michael addition to the 14-membered macrodiolide, which was inspired by plausible biosynthetic pathways. This approach succeeded in the construction of the acaulide skeleton, which revealed the specific conformation of the 14-membered macrodiolide for late stage functionalization.

Authors+Show Affiliations

Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan. Center for Research and Education on Drug Discovery, Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan. Center for Research and Education on Drug Discovery, Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan. Center for Research and Education on Drug Discovery, Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan. Global Station for Biosurfaces and Drug Discovery, Global Institution for Collaborative Research and Education (GI-CoRE), Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32619097

Citation

Hirabayashi, Jun, et al. "Total Synthesis of Acaulide and Acaulone A." Organic Letters, vol. 22, no. 14, 2020, pp. 5545-5549.
Hirabayashi J, Yakushiji F, Katsuyama A, et al. Total Synthesis of Acaulide and Acaulone A. Org Lett. 2020;22(14):5545-5549.
Hirabayashi, J., Yakushiji, F., Katsuyama, A., & Ichikawa, S. (2020). Total Synthesis of Acaulide and Acaulone A. Organic Letters, 22(14), 5545-5549. https://doi.org/10.1021/acs.orglett.0c01907
Hirabayashi J, et al. Total Synthesis of Acaulide and Acaulone A. Org Lett. 2020 Jul 17;22(14):5545-5549. PubMed PMID: 32619097.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Total Synthesis of Acaulide and Acaulone A. AU - Hirabayashi,Jun, AU - Yakushiji,Fumika, AU - Katsuyama,Akira, AU - Ichikawa,Satoshi, Y1 - 2020/07/03/ PY - 2020/7/4/pubmed PY - 2020/7/4/medline PY - 2020/7/4/entrez SP - 5545 EP - 5549 JF - Organic letters JO - Org. Lett. VL - 22 IS - 14 N2 - Acaulide and acaulone A, which contain 14-membered macrodiolides, were isolated from a culture of Acaulium sp. H-JQSF. The antiosteoporosis activity of acaulide is expected to contribute to drug discovery research for an aging society. We herein report the first total synthesis of acaulide, acaulone A, and 10-keto-acaudiol A. Acaulide and acaulone A were synthesized via the late stage Michael addition to the 14-membered macrodiolide, which was inspired by plausible biosynthetic pathways. This approach succeeded in the construction of the acaulide skeleton, which revealed the specific conformation of the 14-membered macrodiolide for late stage functionalization. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/32619097/Total_Synthesis_of_Acaulide_and_Acaulone_A L2 - https://doi.org/10.1021/acs.orglett.0c01907 DB - PRIME DP - Unbound Medicine ER -
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