Journal ArticleDOI
Enantioselective Total Synthesis of ( – )-Spiroxins A, C and D
TLDR
In this article, a scalable enantioselective epoxidation of 5-substituted naphthoquinone, an oxidation/spiroketalization cascade, ortho-selective chlorination of phenol unit and oxime ester-directed acetoxylation, a divergent and enanti-lective synthetic route to (-)-spiroxins A and C and the first total synthesis of (-)-SPiroxin D have been achieved.Abstract:
Spiroxins A, C and D are metabolites with unique polycyclic structures and intriguing biological activities. Based on a scalable enantioselective epoxidation of 5-substituted naphthoquinone, an oxidation/spiroketalization cascade, ortho -selective chlorination of phenol unit and oxime ester-directed acetoxylation, a divergent and enantioselective synthetic route to (-)-spiroxins A and C and the first total synthesis of (-)-spiroxin D have been achieved. The synthetic compounds provide a good foundation for the investigation of antitumor activity and antibacterial activity of the natural products and their synthetic intermediates.read more
Citations
More filters
Journal ArticleDOI
Marine natural products.
TL;DR: A review of the literature published in 2020 for marine natural products (MNPs), with 757 citations (747 for the period January to December 2020) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms as discussed by the authors .
Journal ArticleDOI
Total synthesis, structure revision and cytotoxic activity of Sch 53825 and its derivatives
TL;DR: The first total synthesis of Sch 53825 was achieved in 12 steps from 5-hydroxy-1-tetralone in 16% overall yield through N-benzyl cinchoninium chloride-catalyzed asymmetric epoxidation and a Mitsunobu reaction as the key steps.
Journal ArticleDOI
Synthesis of Complex Dihydroisoquinolin Derivatives via Cobalt‐Electrocatalyzed C−H Activation
Lin Dong,Ying-hui Huang +1 more
Journal ArticleDOI
Investigations on Biomimetic Dimerization in Natural Product Synthesis
TL;DR: In this article , a summary of biomimetic dimerization in natural product synthesis has been summarized, which includes synthetic exploration of linderaspirone A, bi-linderone, parvistemin A, (±)-diperezone, scabellone B, and spiroxins A/C/D.
References
More filters
Journal ArticleDOI
Palladium-Catalyzed Oxygenation of Unactivated sp3 C−H Bonds
TL;DR: A new palladium-catalyzed method for the oxygenation of unactivated sp3 C-H bonds is described, and the high selectivities are rationalized on the basis of the requirements of putative palladium alkyl intermediates.
Journal ArticleDOI
A Rational Approach to Catalytic Enantioselective Enolate Alkylation Using a Structurally Rigidified and Defined Chiral Quaternary Ammonium Salt under Phase Transfer Conditions
Journal ArticleDOI
Marine Pharmacology in 2009–2011: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, and Antiviral Activities; Affecting the Immune and Nervous Systems, and other Miscellaneous Mechanisms of Action
TL;DR: The peer-reviewed marine pharmacology literature from 2009 to 2011 is presented in this review, following the format used in the 1998–2008 reviews, and the pharmacology of structurally-characterized compounds isolated from marine animals, algae, fungi and bacteria is discussed in a comprehensive manner.
Journal ArticleDOI
Oxone as an inexpensive, safe, and environmentally benign oxidant for C-H bond oxygenation.
TL;DR: Peroxide-based oxidants in the Pd(OAc)(2)-catalyzed acetoxylation and etherification of arene and alkane C-H bonds proved particularly effective, and these transformations were applied to a wide variety of substrates.