A concise total synthesis of 11-O-methyldebenzoyltashironin is reported in which oxidative dearomatization-IMDA-RCM triad constitutes the key ring forming steps, while an unorthodox DIBAL-H mediated ...stereo- and regioselective reductive epoxide openings and implementation of the vinyl bromide-carbonyl equivalency concept were pivotal to the success of this endeavor.
In an approach directed toward a tashironin based complex natural product, efficacy of the singlet oxygen mediated 4+2-cycloaddition to a tetracyclic cyclopentadiene has been evaluated to install the ...key
cis-1,4-dihydroxy functionality.
Synthetic studies directed towards allo-cedrane based, tashironin sibling natural products, involving some deft functional group manipulations on a preformed tetracyclic scaffold, are delineated.
α-Stannylated and α-iodinated enamides can easily be obtained by molybdenum-catalyzed regio- and stereoselective hydrostannation and subsequent tin–iodine exchange. These functionalized enamides are ...interesting building blocks for a wide range of cross-coupling reactions giving access to various types of α-substituted enamides.
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Novel imidazole-based ketene dithioacetals show impressive in planta activity against the economically important plant pathogens Alternaria solani, Botryotinia fuckeliana, Erysiphe ...necator and Zymoseptoria tritici. Especially derivatives of the topical antifungal lanoconazole, which bear an alkynyloxy or a heteroaryl group in the para-position of the phenyl ring, exhibit excellent control of the mentioned phytopathogens. These compounds inhibit 14α -demethylase in the sterol biosynthesis pathway of the fungi. Synthesis routes starting from either benzaldehydes or acetophenones as well as structure-activity relationships are discussed in detail.
A two-step protocol based on tandem Wessely oxidation/intramolecular Diels–Alder reaction to provide general access to the 3-prenyl-4-oxa-tricyclo4.3.1.0
3,7dec-8-en-2-one core present in the caged
...Garcinia xanthonoids is demonstrated. These readily accessible tricyclic scaffolds also provide ready entry into a variety of substituted γ-lactones through a photochemical 1,3-acyl shift and decarbonylation.
An exceptionally short (three step) strategy involving tandem oxidative dearomatization, intramolecular Diels–Alder (IMDA) reaction and RCM has been devised to generate the complete carbon framework ...present in tashironin-type sesquiterpenoid natural products.
