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 ◽  
...  

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.

2008 ◽  
Vol 10 (22) ◽  
pp. 5239-5242 ◽  
Author(s):  
Shinsuke Inuki ◽  
Shinya Oishi ◽  
Nobutaka Fujii ◽  
Hiroaki Ohno

2021 ◽  
Author(s):  
Zhen Zhang ◽  
Sneha Ray ◽  
Leah Imlay ◽  
Lauren Callaghan ◽  
Hanspeter Niederstrasser ◽  
...  

<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>


2011 ◽  
Vol 83 (3) ◽  
pp. 507-518 ◽  
Author(s):  
Christine Beemelmanns ◽  
Hans-Ulrich Reissig

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.


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

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

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