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通过 BINOL-磷酸催化的串联氧化环化反应全合成(±)-decursivine。

Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization.

机构信息

Department of Chemistry and Chemical Biology, Northeastern University, 102 Hurtig Hall, 360 Huntington Avenue, Boston, MA, 02115, USA.

Department of Pharmaceutical Sciences, Northeastern University, 102 Hurtig Hall, 360 Huntington Avenue, Boston, MA, 02115, USA.

出版信息

Sci Rep. 2021 Oct 7;11(1):19915. doi: 10.1038/s41598-021-99064-8.

DOI:10.1038/s41598-021-99064-8
PMID:34620892
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8497573/
Abstract

The synthesis of tetracyclic indole alkaloid (±)-decursivine was accomplished using BINOL-phosphoric acid catalyzed tandem oxidative cyclization as a key step with (bis(trifluoroacetoxy)iodo)benzene (PIFA) as an oxidizing agent. This represents one of the shortest and highest yielding routes for the synthesis of (±)-decursivine from readily available starting materials.

摘要

四元吲哚生物碱(±)-去甲骆驼蓬碱的合成都使用了 BINOL-磷酸催化的串联氧化环化作为关键步骤,其中(双(三氟乙酰氧基)碘)苯(PIFA)作为氧化剂。这是从易得的起始原料合成(±)-去甲骆驼蓬碱的最短和最高收率路线之一。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37b5/8497573/7676187585a3/41598_2021_99064_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37b5/8497573/09af227257ec/41598_2021_99064_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37b5/8497573/44a18060f9ab/41598_2021_99064_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37b5/8497573/28d0ca18a5c5/41598_2021_99064_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37b5/8497573/d35d2e444328/41598_2021_99064_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37b5/8497573/7676187585a3/41598_2021_99064_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37b5/8497573/09af227257ec/41598_2021_99064_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37b5/8497573/44a18060f9ab/41598_2021_99064_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37b5/8497573/28d0ca18a5c5/41598_2021_99064_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37b5/8497573/d35d2e444328/41598_2021_99064_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37b5/8497573/7676187585a3/41598_2021_99064_Fig5_HTML.jpg

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