Journal ArticleDOI
Protecting-group-free synthesis of taiwaniaquinone H using a one-pot thermal ring expansion/4π-electrocyclization strategy.
Xiuxiang Yan,Xiangdong Hu +1 more
TLDR
The efficiency of the one-pot thermal ring expansion/4π-electrocyclization process has been demonstrated through its application in the total synthesis of taiwaniaquinone H, which has been accomplished in three steps and 14% overall yield in a protecting-group-free manner starting from commercially available materials.Abstract:
A strategy to the 6-5-6 tricyclic scaffold of taiwaniaquinoids was established on the basis of a one-pot thermal ring expansion/4π-electrocyclization process. The efficiency of this methodology has been demonstrated through its application in the total synthesis of taiwaniaquinone H, which has been accomplished in three steps and 14% overall yield in a protecting-group-free manner starting from commercially available materials.read more
Citations
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Journal ArticleDOI
Total Synthesis of Taiwaniadducts B, C, and D
TL;DR: The first total syntheses of taiwaniadducts B, C, and D have been accomplished, and two diterpenoid segments were prepared with high enantiopurity, both through Ir-catalyzed asymmetric polyene cyclization.
Journal ArticleDOI
Nazarov reaction: current trends and recent advances in the synthesis of natural compounds and their analogs
TL;DR: The Nazarov reaction (cyclization) is one of the most useful synthetic tools for the stereoselective preparation of various cyclopentenone scaffolds and recent applications are summarized.
Journal ArticleDOI
Palladium‐Catalyzed α‐Arylation Reactions in Total Synthesis
Sudheesh T. Sivanandan,Ashna Shaji,Ibrahim Ibnusaud,Carin C. C. Johansson Seechurn,Thomas J. Colacot +4 more
TL;DR: The development of palladium-catalyzed α-arylation of carbonyl compounds has emerged as a new avenue in the design of new routes for the synthesis of natural products and active pharmaceutical ingredients (APIs) as discussed by the authors.
Journal ArticleDOI
Recent advances of synthesis of fluorenone and fluorene containing natural products
Yingbo Shi,Shuanhu Gao +1 more
Journal ArticleDOI
Electrochemical Deprotection of para-Methoxybenzyl Ethers in a Flow Electrolysis Cell
Robert A. Green,Katherine E. Jolley,Azzam A. M. Al-Hadedi,Derek Pletcher,David C. Harrowven,Oscar de Frutos,Carlos Mateos,David J. Klauber,Juan A. Rincón,Richard C. D. Brown +9 more
TL;DR: Electrochemical deprotection of PMB ethers was performed in an undivided electrochemical flow reactor in MeOH solution, leading to the unmasked alcohol and p-methoxybenzaldehyde dimethyl acetal as a byproduct, removing the need for chemical oxidants.
References
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Journal ArticleDOI
The catalytic enantioselective, protecting group-free total synthesis of (+)-dichroanone.
Ryan M. McFadden,Brian M. Stoltz +1 more
TL;DR: This 11-step preparation of the molecule from commercial material features a novel Kumada-aromatization strategy and a rapid sequence for the conversion of a phenol to a hydroxy-p-benzoquinone.
Journal ArticleDOI
The taiwaniaquinoids: a review.
George Majetich,Joel M. Shimkus +1 more
TL;DR: This review covers the literature from the discovery of the first taiwaniaquinoid in 1995 until June 2009 and a detailed discussion of 12 published syntheses of members of this family of natural products is presented.
Journal ArticleDOI
Conjugated ketenes: new aspects of their synthesis and selected utility for the synthesis of phenols, hydroquinones, and quinones
Journal ArticleDOI
A general, regiospecific synthesis of highly substituted quinones
Journal ArticleDOI
Synthesis of Taiwaniaquinoids via Nazarov Triflation
TL;DR: A new variant of the Nazarov reaction with concomitant formation of an enol triflate serves as one of the key steps, considerably shortening the synthetic scheme and providing a general entry into this class of bioactive natural products.