Total Syntheses of the Tetracyclic Cyclopiane Diterpenes Conidiogenone, Conidiogenol, and Conidiogenone B

Hou, Si‐Hua; Tu, Yong‐Qiang; Wang, Shuanghu; Xi, Chao-Chao; Zhang, Fu‐Min; Wang, Shaohua; Li, Yantao; Liu, Lin

doi:10.1002/ange.201600529

Cited by 13 publications

(1 citation statement)

References 40 publications

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“…Conidiogenone C 8 showed potent cytotoxicity against HL-60 and BEL-7402 cell lines with IC 50 values of 0.038 and 0.97 μM, and conidiogenone G 12 showed potent cytotoxicity against HL-60 cell line with an IC 50 value of 1.1 μM [ 72 ]. Provoked by the novelty of structures and potent bioactivities, total syntheses of 1 , 6 , and 7 were achieved, which led to further determination of their absolute configurations [ 74 ].…”

Section: Cyclopianementioning

confidence: 99%

Diterpenes Specially Produced by Fungi: Structures, Biological Activities, and Biosynthesis (2010–2020)

Zhang

Feng

2022

JoF

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Fungi have traditionally been a very rewarding source of biologically active natural products, while diterpenoids from fungi, such as the cyathane-type diterpenoids from Cyathus and Hericium sp., the fusicoccane-type diterpenoids from Fusicoccum and Alternaria sp., the guanacastane-type diterpenoids from Coprinus and Cercospora sp., and the harziene-type diterpenoids from Trichoderma sp., often represent unique carbon skeletons as well as diverse biological functions. The abundances of novel skeletons, biological activities, and biosynthetic pathways present new opportunities for drug discovery, genome mining, and enzymology. In addition, diterpenoids peculiar to fungi also reveal the possibility of differing biological evolution, although they have similar biosynthetic pathways. In this review, we provide an overview about the structures, biological activities, evolution, organic synthesis, and biosynthesis of diterpenoids that have been specially produced by fungi from 2010 to 2020. We hope this review provides timely illumination and beneficial guidance for future research works of scholars who are interested in this area.

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Section: Cyclopianementioning

confidence: 99%

Diterpenes Specially Produced by Fungi: Structures, Biological Activities, and Biosynthesis (2010–2020)

Zhang

Feng

2022

JoF

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Total Syntheses of (−)‐Conidiogenone B, (−)‐Conidiogenone, and (−)‐Conidiogenol

Xun

et al. 2020

Angewandte Chemie

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Cyclopianes are novel diterpenes featuring a highly strained 6/5/5/5 tetracyclic core embedded with 6–8 consecutive stereocenters. The concise total syntheses of (−)‐conidiogenone B, (−)‐conidiogenone, and (−)‐conidiogenol have been accomplished in 14–17 steps. The present work features a HAT‐mediated alkene–nitrile cyclization to access the cis‐biquinane, a Nicholas/Pauson–Khand reaction to construct the linear triquinane, and a Danheiser annulation to afford the congested angular triquinane skeleton.

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Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler–Napieralski/Semipinacol Rearrangement Reaction

Wang

Zhuang

et al. 2020

Angewandte Chemie

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A tandem Bischler-Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine-type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction to expeditiously construct the central bridged bicyclo[2.2.1]heptane ring system of these molecules with contiguous quaternary centers. The development of this novel strategy culminated in the collective total synthesis of four aspidofractinine alkaloids.

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Total Syntheses of the Tetracyclic Cyclopiane Diterpenes Conidiogenone, Conidiogenol, and Conidiogenone B

Abstract: Scheme 2. Retrosynthetic analysis of 1-3.TMS = trimethylsilyl. Angewandte Chemie Communications

Cited by 13 publications

References 40 publications

Diterpenes Specially Produced by Fungi: Structures, Biological Activities, and Biosynthesis (2010–2020)

Diterpenes Specially Produced by Fungi: Structures, Biological Activities, and Biosynthesis (2010–2020)

Total Syntheses of (−)‐Conidiogenone B, (−)‐Conidiogenone, and (−)‐Conidiogenol

Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler–Napieralski/Semipinacol Rearrangement Reaction

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