scholarly journals Second Generation Synthesis of the Neo-Clerodane Diterpenoid Methyl Barbascoate

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Hisahiro Hagiwara ◽  
Naomi Honma ◽  
Kimihiko Kinugawa ◽  
Shota Sato ◽  
Takashi Hoshi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Second Generation ◽  
Samarium Diiodide ◽  
Conjugate Reduction ◽  
Palladium Catalyzed ◽  
Clerodane Diterpenoid

The second generation total synthesis of the neo-clerodane diterpenoid, methyl barbascoate, was accomplished in seven or nine linear steps via double enol triflation and subsequent palladium catalyzed double carbonylation, followed by regioselective samarium diiodide mediated conjugate reduction.

scholarly journals Total Synthesis of (±)-Lysergic Acid, Lysergol, and Isolysergol by Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group

2008 ◽  
Vol 10 (22) ◽  
pp. 5239-5242 ◽  
Author(s):  
Shinsuke Inuki ◽  
Shinya Oishi ◽  
Nobutaka Fujii ◽  
Hiroaki Ohno
Keyword(s):  
Total Synthesis ◽  
Lysergic Acid ◽  
Palladium Catalyzed

scholarly journals Total Synthesis of (+)-Spiroindimicin A via Asymmetric Palladium-Catalyzed Spirocyclization

2021 ◽  
Author(s):  
Zhen Zhang ◽  
Sneha Ray ◽  
Leah Imlay ◽  
Lauren Callaghan ◽  
Hanspeter Niederstrasser ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Human Health ◽  
Neglected Tropical Diseases ◽  
Indole Alkaloids ◽  
Sleeping Sickness ◽  
Tropical Diseases ◽  
African Sleeping Sickness ◽  
Palladium Catalyzed ◽  
Natural Precursor

<p>The spiroindimicins are a unique class of chlorinated indole alkaloids characterized by three heteroaromatic rings structured around a congested spirocyclic stereocenter. Here, we report the first total synthesis of (+)-spiroindimicin A, which bears a challenging C-3’/C-5’’-linked spiroindolenine. We detail our initial efforts to effect a biomimetic oxidative spirocyclization from its proposed natural precursor, lynamicin D, and describe how these studies shaped our final abiotic 9-step solution to this complex alkaloid built around a key asymmetric Pd-catalyzed spirocyclization. Scalable access to spiroindimicins A, H, and their congeners has enabled discovery of their activity against several parasites relevant to human health, providing potential starting points for new therapeutics for the neglected tropical diseases leishmaniasis and African sleeping sickness.</p>

New samarium diiodide-induced cyclizations

2011 ◽  
Vol 83 (3) ◽  
pp. 507-518 ◽  
Author(s):  
Christine Beemelmanns ◽  
Hans-Ulrich Reissig
Keyword(s):  
Total Synthesis ◽  
Carbonyl Compounds ◽  
Samarium Diiodide

Samarium diiodide (SmI2) smoothly promotes the cyclizations of suitably substituted carbonyl compounds with styrene subunits leading to benzannulated cyclooctenes. The intramolecular samarium ketyl addition to arene or hetarene moieties enables a new, efficient, and highly stereoselective entry to dearomatized products such as hexahydronaphthalenes, steroid-like tetra- or pentacyclic compounds, or dihydroindole derivatives. The usefulness of the developed SmI2-induced cyclization method was demonstrated by the shortest formal total synthesis of the alkaloid strychnine.

Second-generation total synthesis of (−)-diversifolin

2010 ◽  
Vol 51 (14) ◽  
pp. 1876-1879 ◽  
Author(s):  
Kazuma Tsuboi ◽  
Tomoaki Nakamura ◽  
Takahiro Suzuki ◽  
Atsuo Nakazaki ◽  
Susumu Kobayashi
Keyword(s):  
Total Synthesis ◽  
Second Generation

ChemInform Abstract: Application of the Palladium-Catalyzed Norbornene-Assisted Catellani Reaction Towards the Total Synthesis of (+)-Linoxepin (V) and Isolinoxepin (VI).

ChemInform ◽  
2015 ◽  
Vol 46 (6) ◽  
pp. no-no
Author(s):  
Zafar Qureshi ◽  
Harald Weinstabl ◽  
Marcel Suhartono ◽  
Hongqiang Liu ◽  
Pierre Thesmar ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Palladium Catalyzed
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