Total syntheses of dehydrobotrydienal, dehydrobotrydienol and 10-oxodehydrodihydrobotrydial

Zhang, Zichun; Zhao, Dandan; He, Yingdong; Yang, Zhen; Gong, Jianxian

doi:10.1016/j.cclet.2019.03.033

Cited by 8 publications

(2 citation statements)

References 23 publications

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“…As a common intermediate, ketone 118 was transformed to 4- epi -presilphiperfolan-8β-ol (119) and 7- epi -presilphiperfolan-1β-ol (120) in a few steps reaction. Next year, Yang and Gong ( Zhang et al, 2019 ) continued their previous work by the Co-TMTU-catalyzed tandem Pauson-Khand and 6π-electrocyclizationreactions, the total syntheses of three botryane sesquiterpenoids: dehydrobotrydienal (122), dehydrobotrydienol (124) and 10-oxodehydrodihydrobotrydial (125) were delivered from the common intermediate 118.…”

Section: The Total Synthesis Of Terpenoid Enabled By Cobalt-catalyzedmentioning

confidence: 99%

Total Synthesis of Natural Terpenoids Enabled by Cobalt Catalysis

Shu

Ai²,

Liu³

et al. 2022

Front. Chem.

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Transition metal catalysis plays an essential role in the total synthesis of natural products. Cobalt-mediated asymmetric catalysis has successfully been used as a primary or a secondary step in the total synthesis of natural products, especially terpenoids. Terpenoids represent one of the most prominent families among various categories of natural products, attracting immense attention due to their promising physiological activities. This review summarizes the recent advances toward the total synthesis of terpenoids by cobalt-mediated asymmetric catalysis, which may shed some light on their future synthetic efforts toward natural pesticides such as celanguline, azadirachtin, etc.

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Section: The Total Synthesis Of Terpenoid Enabled By Cobalt-catalyzedmentioning

confidence: 99%

Total Synthesis of Natural Terpenoids Enabled by Cobalt Catalysis

Shu

Ai²,

Liu³

et al. 2022

Front. Chem.

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“…The obtained tricyclic product can be converted to two presilphiperfolanols and several other tricyclic derivatives. Through ring-opening reactions and functionalizations of this tricyclic product, they (Zhang et al, 2019) recently achieved total syntheses of three sesquiterpenoids, which enriched the application of this reaction. The above works show great potential for expanding the application of Pauson-Khand reaction with other types of reactions especially pericyclic reactions.…”

Section: Construction Of Polycyclic Carbocyclesmentioning

confidence: 99%

Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation

Zheng

Hua

2020

Front. Chem.

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Polycyclic scaffolds are omnipresent in natural products and drugs, and the synthetic strategies and methods toward construction of these scaffolds are of particular importance. Compared to simple cyclic ring systems, polycyclic scaffolds have higher structure complexity and diversity, making them suitable for charting broader chemical space, yet bringing challenges for the syntheses. In this review, we surveyed progress in the past decade on synthetic methods for polycyclic natural product scaffolds, in which the key steps are one-pot reactions involving intermolecular or intramolecular alkyne annulation. Synthetic strategies of selected polycyclic carbocycles and heterocycles with at least three fused, bridged, or spiro rings are discussed with emphasis on the synthetic efficiency and product diversity. Recent examples containing newly developed synthetic concepts or toolkits such as collective and divergent total synthesis, gold catalysis, C-H functionalization, and dearomative cyclization are highlighted. Finally, several "privileged synthetic strategies" for "privileged polycyclic scaffolds" are summarized, with discussion of remained challenges and future perspectives.

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Four‐Step Synthesis of (−)‐4‐epi‐Presilphiperfolan‐8α‐ol by Intramolecular Iron Hydride Atom Transfer‐Mediated Ketone‐Alkene Coupling and Studies to Accesstrans‐Hydrindanols with a Botryane Scaffold

Saladrigas

Gómez‐Bengoa

Bonjoch

et al. 2023

Chemistry A European J

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From an (R)‐(+)‐pulegone‐derived building block that incorporates the stereo‐defined tertiary carbon bearing a methyl group, as found in the targeted sesquiterpenoid, a four‐step synthesis of (−)‐4‐epi‐presilphiperfolan‐8‐α‐ol was achieved. The key processes involved are a ring‐closing metathesis leading to a bridged alkene‐tethered ketone and its subsequent FeIII‐mediated metal‐hydride atom transfer (MHAT) transannular cyclization. This synthetic method, implying an irreversible addition of a carbon‐centered radical upon a ketone by means of a hydrogen atom transfer upon the alkoxy radical intermediate, was also applied in the synthesis of trans‐fused hydrindanols structurally related to botrydial compounds.

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Total syntheses of dehydrobotrydienal, dehydrobotrydienol and 10-oxodehydrodihydrobotrydial

Cited by 8 publications

References 23 publications

Total Synthesis of Natural Terpenoids Enabled by Cobalt Catalysis

Total Synthesis of Natural Terpenoids Enabled by Cobalt Catalysis

Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation

Four‐Step Synthesis of (−)‐4‐epi‐Presilphiperfolan‐8α‐ol by Intramolecular Iron Hydride Atom Transfer‐Mediated Ketone‐Alkene Coupling and Studies to Accesstrans‐Hydrindanols with a Botryane Scaffold

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