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Title: Total Synthesis of Lyconesidine B, a Lycopodium Alkaloid with an Oxygenated, Amine-Type Fawcettimine Core
Authors: Kurose, Tomohiro
Tsukano, Chihiro  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-9361-0857 (unconfirmed)
Nanjo, Takeshi  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-5679-6701 (unconfirmed)
Takemoto, Yoshiji  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0003-1375-3821 (unconfirmed)
Author's alias: 黒瀬, 朋浩
塚野, 千尋
南條, 毅
竹本, 佳司
Keywords: Catalysts
Organic synthesis
Organic compounds
Cyclization
Chemical synthesis
Issue Date: Feb-2021
Publisher: American Chemical Society (ACS)
Journal title: Organic Letters
Volume: 23
Issue: 3
Start page: 676
End page: 681
Abstract: This report describes the total synthesis of the complex, oxygenated tetracyclic alkaloid, lyconesidine B. The key synthetic challenge involves diastereoselective generation of a decahydroquinoline ring with a quaternary carbon at the angular position via domino cyclopropanation, ring-opening, and reduction. Another crucial step is the domino ene-yne metathesis involving a quaternary ammonium ion, leading to the construction of a decahydroazaazulen framework.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.0c03816.
The full-text file will be made open to the public on December 16, 2021 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/266607
DOI(Published Version): 10.1021/acs.orglett.0c03816
PubMed ID: 33325708
Appears in Collections:Journal Articles

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