Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C14‑epi-deoxycalyciphylline H

Hu，Jingping; Xu，Jing

2024-04-01

10.1016/j.cclet.2023.108733

Chinese Chemical Letters   影响因子和分区

1001-8417

One of the largest subfamilies within the famous Daphniphyllum alkaloid family is made up of the yuzurimine-type (or macrodaphniphyllamine-type) alkaloids. Their complex aza-polycyclic caged structures, several contiguous stereogenic centers, and vicinal all-carbon quaternary centers make these alkaloids formidable challenge for synthetic chemists. Recently, synthesis of these alkaloids has received extensive attention from our community. Herein, we wish to report the total synthesis of C‑epi-deoxycalyciphylline H, a putative member of yuzurimine-type alkaloid subfamily. Key transformations employed in our approach include an intramolecular Prins reaction and a Pd-catalyzed enyne cycloisomerization. In addition, synthesis of a daphnezomine L-type alkaloid, paxdaphnidine A, was also studied.

Daphniphyllum alkaloids Enyne cycloisomerization Prins reaction Total synthesis Yuzurimine-type alkaloids

SCI

英语

第一 ; 通讯

CHEMISTRY

2-s2.0-85183135086

Scopus

Shenzhen Grubbs Institute and Department of Chemistry and Guangdong Provincial Key Laboratory of Catalysis and Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis,Southern University of Science and Technology,Shenzhen,518055,China

Hu，Jingping,Xu，Jing. Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C14‑epi-deoxycalyciphylline H[J]. Chinese Chemical Letters,2024,35(4).

Hu，Jingping,&Xu，Jing.(2024).Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C14‑epi-deoxycalyciphylline H.Chinese Chemical Letters,35(4).

Hu，Jingping,et al."Total synthesis of a putative yuzurimine-type Daphniphyllum alkaloid C14‑epi-deoxycalyciphylline H".Chinese Chemical Letters 35.4(2024).