(1R,4S,5S)-5-((3-Hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol

Abstract

Using environmentally friendly conditions, the nucleophilic ring-opening reaction of 6-azabicyclo[3.1.0]hex-3-en-2-ol with 1-methyl-1H-tetrazole-5-thiol provided a novel thiol-incorporated aminocyclopentitol, (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol, in excellent yield (95%). The newly synthesized compound was analyzed and characterized via 1H, 13C-NMR, HSQC, and mass spectral data.

Combining photochemical transformation of pyridinium salt with kinetic enzymatic resolution towards the total synthesis of (-)-agelastatin A

“…30,31 Our retrosynthetic analysis has as key compound the bicyclic vinyl azirine II, a versatile molecule for which we have recently developed a flow methodology for multigram scale synthesis from the photoirradiation of cheap and easily obtained pyridinium salts I. 31,32 Molecule II already has the cyclopentane C ring of agelastatin A installed, with the carbon steroecenters with the right relative configuration. Combined with an enzymatic kinetic resolution, exploiting the free alcohol of II, the key synthon II could be obtained enantiomerically pure in large quantities via enantioselective acetylation.…”

Nitrogen-Containing Molecules: Natural and Synthetic Products including Coordination Compounds

“…The majority (13) of the published content was in the field of synthetic chemistry, including synthetic methodologies and studies on chemical reactions and reactivity, while two papers dealt with coordination chemistry and one with structural elucidation. In particular, contributions related to organic synthesis may be divided in the subfields of aromatic reactivity (2), reactivity of heterocycles (2), synthesis of heterocycles (6), and detailed routine synthesis of very important compounds (3). Two of these papers included biological evaluation experiments.…”

“…The reaction occurred under mild conditions (37 • C, water) and according to authors' claims, in a regio-and stereospecific manner. The product can be readily further functionalized via its primary and secondary hydroxyl groups [6].…”