584-00-9

Usage

InChI:InChI=1/C5H8O/c1-3-5(2)4-6/h1,5-6H,4H2,2H3

Upstream product

• 113647-42-0 3-Bromo-but-1-yne 
• 50-00-0 formaldehyd 
• 195062-82-9 (S)-3-tert-butyl dimethyl(2-methylbut-3-ynyloxyl)silane 
• 89489-98-5 ethyl 1,2-butadienyl sulfide 

Downstream Products

• 151370-42-2 C₁₅H₂₄OSi₂ 
• 598-23-2 3-methyl-but-1-yne 
• 126856-28-8 3-bromo-3,4-dihydro-2,2-dimethyl-6-phenylsulfonyl-2H-benzo[b]pyran-4-ol 
• 102356-91-2 2-<3-(4'-chlorobenzoyl)isoxazol-5-yl>propionic acid 
• 151370-56-8 (Z)-3-<(dimethylphenylsilyl)methylene>-2,2,4-trimethyl-1,2-oxasilolane 

Relevant academic research and scientific papers

ANTIBACTERIAL AGENTS

Antibacterial compounds of formula (I) are provided, as well as stereoisomers and pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.

Total synthesis of the spirocyclic imine marine toxin (-)-gymnodimine and an unnatural C4-epimer

The first total synthesis of the marine toxin (-)-gymnodimine (1) has been accomplished in a convergent manner. A highly diastereo- and enantioselective exo-Diels-Alder reaction catalyzed by a bis-oxazoline Cu(II) catalyst enabled rapid assembly of the spirocyclic core of gymnodimine. The preparation of the tetrahydrofuran fragment utilized a chiral auxiliary based anti-aldol reaction. Two major fragments, spirolactam 56 and tetrahydrofuran 55, were then coupled through an efficient Nozaki-Hiyama-Kishi reaction. An unconventional, ambient temperature t-BuLi-initiated intramolecular Barbier reaction of alkyl iodide 64 was employed to form the macrocycle. A late stage vinylogous Mukaiyama aldol addition of a silyloxyfuran to a complex cyclohexanone 83 appended the butenolide, and a few additional steps provided (-)-gymnodimine (1). A diastereomer of the natural product was also synthesized, C4-epi-gymnodimine (90), derived from the vinylogous Mukaiyama aldol addition.

Electrocyclic ring closure of the enols of vinyl quinones. A 2H-chromene synthesis

equation presented Thermolysis of enolizable vinyl quinones in polar, aprotic media provides 2H-chromenes. Experimental evidence supports a two-step mechanism in which enolization is followed by a thermal 6π-electrocyclic reaction of an intermediate quinone methide. Application of this method led to the total synthesis of the reputed structure of an Ageratum juvenile hormone. When enolizable vinyl quinones are the products of Stille coupling, the chromene annulation product is obtained directly.