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Keywords = waihoensene

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48 pages, 24987 KiB  
Review
Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review
by Sana Sikandar, Ameer Fawad Zahoor, Abdul Ghaffar, Muhammad Naveed Anjum, Razia Noreen, Ali Irfan, Bushra Munir, Katarzyna Kotwica-Mojzych and Mariusz Mojzych
Molecules 2023, 28(2), 704; https://doi.org/10.3390/molecules28020704 - 10 Jan 2023
Cited by 9 | Viewed by 5296
Abstract
Allenes with two carbon–carbon double bonds belong to a unique class of unsaturated hydrocarbons. The central carbon atom of allene is sp hybridized and forms two σ-bonds and two π-bonds with two terminal sp2 hybridized carbon atoms. The chemistry of allenes has [...] Read more.
Allenes with two carbon–carbon double bonds belong to a unique class of unsaturated hydrocarbons. The central carbon atom of allene is sp hybridized and forms two σ-bonds and two π-bonds with two terminal sp2 hybridized carbon atoms. The chemistry of allenes has been well documented over the last decades. They are more reactive than alkenes due to higher strain and exhibit significant axial chirality, thus playing a vital role in asymmetric synthesis. Over a variety of organic transformations, allenes specifically undergo classical metal catalyzed cycloaddition reactions to obtain chemo-, regio- and stereoselective cycloadducts. This review briefly describes different types of annulations including [2+2], [2+2+1], [3+2], [2+2+2], [4+2], [5+2], [6+2] cycloadditions using titanium, cobalt, rhodium, nickel, palladium, platinum, gold and phosphine catalyzed reactions along with a mechanistic study of some highlighted protocols. The synthetic applications of these reactions towards the synthesis of natural products such as aristeromycin, ent-[3]-ladderanol, waihoensene(−)-vindoline and (+)-4-epi-vindoline have also been described. Full article
(This article belongs to the Special Issue Design, Synthesis, and Analysis of Potential Drugs, 2nd Edition)
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17 pages, 4579 KiB  
Review
Contiguous Quaternary Carbons: A Selection of Total Syntheses
by Alina Eggert, Christoph Etling, Dennis Lübken, Marius Saxarra and Markus Kalesse
Molecules 2020, 25(17), 3841; https://doi.org/10.3390/molecules25173841 - 24 Aug 2020
Cited by 13 | Viewed by 5321
Abstract
Contiguous quaternary carbons in terpene natural products remain a major challenge in total synthesis. Synthetic strategies to overcome this challenge will be a pivotal prerequisite to the medicinal application of natural products and their analogs or derivatives. In this review, we cover syntheses [...] Read more.
Contiguous quaternary carbons in terpene natural products remain a major challenge in total synthesis. Synthetic strategies to overcome this challenge will be a pivotal prerequisite to the medicinal application of natural products and their analogs or derivatives. In this review, we cover syntheses of natural products that exhibit a dense assembly of quaternary carbons and whose syntheses were uncompleted until recently. While discussing their syntheses, we not only cover the most recent total syntheses but also provide an update on the status quo of modern syntheses of complex natural products. Herein, we review (±)-canataxpropellane, (+)-waihoensene, (–)-illisimonin A and (±)-11-O-debenzoyltashironin as prominent examples of natural products bearing contiguous quaternary carbons. Full article
(This article belongs to the Special Issue Natural Product-Inspired Molecules: From Weed to Remedy)
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