Efficient construction of the A/C/D tricyclic skeleton of palhinine A

What is the most favorite and original chemistry developed in your research group? Total synthesis of bioactive natural products is the most favorite chemistry in my research group and development or application of new strategies to improve the synthetic efficiency is the most original chemistry developed in my research group. How do you get into this specific field? Could you please share some experiences with our readers? My PhD project was total synthesis of bioactive natural lignans and I devoted myself into synthetic methodology development during my postdoctoral research period. In my opinion, a highly efficient synthetic method will greatly shorten the synthetic route and improve its efficiency for a target-oriented total synthesis. On the other hand, target-oriented total synthesis is the best platform to evaluate the practical value of a synthetic method. So I choose total synthesis of natural products and target-oriented synthetic methodology development as my research fields when I began my independent research. How do you supervise your students? When the students start their projects, I discuss the research subjects with them once a month. Every Saturday night we hold a group meeting to learn and discuss the most recent published literatures related to our research. I give more encouragement when the students meet difficulties in their research. Then we try to solve the difficulties together. What is the most important personality for scientific research? In my view, diligence and persistence are the most important personalities for scientific research. What's your hobby? What's your favorite book(s)? Reading. My favorite book is Sapiens-a brief history of humankind. How do you keep balance between research and family? I usually spend six days (from Monday to Saturday) on research work. On Sunday I will cook some delicious food and enjoy it with my family. My wife understands and supports my work very well. She has done a lot for our family.

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“…This high efficient cascade reaction rapidly resulted in a very similar tetracyclic skeleton of palhinine A 52 in 42% yield. [ 23 ]…”

Section: Total Syntheses Of Lycopodium Alkaloidsmentioning

confidence: 99%

Concise Total Syntheses of Bioactive Alkaloids Enabled by Development or Application of Cascade Reactions: A Personnel Adventure

Xie

She

2021

Chin. J. Chem.

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“…Following their successful synthesis in 2012 ( Section 2.1 ), She and coworkers also made many attempts to install the azonane ring on the isotwistane cage, and also encountered great problems. Sandwiching between Fan’s reports in 2016 and 2017, She’s group disclosed their innovative and distinct approach in 2016 [ 19 ]. Different from Fan’s idea, She and coworkers proposed another talent strategy using ring constriction from a large macrocyclic ring system to overcome the inherent strain of the nine-membered medium-sized azonane ring ( Scheme 7 ).…”

Section: Synthetic Efforts Reported During 2016–2020mentioning

confidence: 99%

Strategies and Efforts towards the Total Synthesis of Palhinine Alkaloids

Liang

Gong

et al. 2020

Molecules

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The palhinine family of Lycopodium alkaloids were first reported in 2010, which feature an intriguing isotwistane carbon cage and a nine-membered azonane ring. It is noteworthy that the tetracyclic 5/6/6/9 skeleton was unprecedented in Lycopodium alkaloids before their seminal discovery. Over the past decade, extensive synthetic efforts stemming from seven research groups have resulted in two racemic total syntheses to date. This review article takes the opportunity to survey these efforts and achievements so as to promote further research towards the asymmetric total synthesis of palhinine alkaloids.

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“…Modifying the functional groups on C3 or C6 did not affect the outcome of the reaction. Previous synthetic studies of the palhinines concluded that the twisted structure of the isotwistane moiety may strain the 9-membered fused ring at its bridgeheads (C4 and C12).…”

mentioning

confidence: 99%

Influence of Ring Strain on the Formation of Rearrangement vs Cyclization Isotwistane Products in the Acyl Radical Reaction of Bicyclo[2.2.2]octanone

Chen,

Lin,

Hsieh

et al. 2023

Org. Lett.

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An acyl radical reaction of bicyclo[2.2.2]octenone to yield either rearranged or cyclized isotwistane products is described. The influence of ring strain on the reaction was demonstrated by alternating the sizes of the fused ring in the starting material. DFT calculations showed that the reaction is under thermodynamic control and proceeds via a 5-exo-trig cyclization intermediate, which undergoes either hydrogen-atom transfer (HAT) to give a cyclized product or rearrangement via a twistane intermediate to give a rearranged product.

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Efficient construction of the A/C/D tricyclic skeleton of palhinine A

Abstract: An efficient approach for the synthesis of the 9/6/6 tricyclic structure ofLycopodiumalkaloid palhinine A has been accomplished. This protocol can undergo ring constriction to rapidly construct the highly strained nine-membered azonane ring of palhinine A.

Cited by 14 publications

References 46 publications

Concise Total Syntheses of Bioactive Alkaloids Enabled by Development or Application of Cascade Reactions: A Personnel Adventure

Concise Total Syntheses of Bioactive Alkaloids Enabled by Development or Application of Cascade Reactions: A Personnel Adventure

Strategies and Efforts towards the Total Synthesis of Palhinine Alkaloids

Influence of Ring Strain on the Formation of Rearrangement vs Cyclization Isotwistane Products in the Acyl Radical Reaction of Bicyclo[2.2.2]octanone

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