A new home-made UV photochemical reactor (95 cm of irradiation zone) consisting of a 12 parallel quartz tubes flow reactor, PQT6 (95 cm under irradiation and an internal diameter of 0.6 cm) was assembled to perform photochemical transformations in continuous-flow. PQT6 was evaluated for the photoreaction of 1-allylpyridinium bromide (1a) to 6-allyl-6-azabicyclo[3.1.0]hex-3-en-2-ol (2a), in a continuous process. This technology provides reduced reaction times, continuous production of 2a, and a productivity of 129 mg h−1, corresponding to 1.94 g of isolated 2a after 15 h of irradiation.

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.

(−)‐Agelastatin A was synthetized employing a flow photorearrangement of a pyridinium salt, constructing in one step the cyclopentene core possessing the desired functionalities and relative configurations. A flow enzymatic kinetic resolution of the resulting bicyclic vinyl aziridine delivered the enantiopure precursor to the natural product. This total synthesis required the use of a single protective group. Two novel agelastatin N3‐derivatives were synthesized and their cytotoxicity evaluated against a series of cancer cell lines, which corroborated the importance of unsubstituted N3 in the biological activity of (−)‐agelastatin A.

Agelastatin alkaloids were synthesized through early-stage construction of the synthetically challenging C ring via photochemical transformation of pyridinium salts. Kinetic enzymatic resolution of bicyclic vinyl aziridines allowed the synthesis of (-)-agelastatin A in 4% yield over 12 steps. The cytotoxicity of (±)-agelastatin A and two N3-derivates were tested against a series of cancer cell lines to evaluate the impact of N3-substituition of the biological activity of agelastatin derivatives and corroborated the importance of unsubstituted N3 in the cytotoxicity of (-)-agelastatin A.

α-hydroxycixlopenteno-aziridines are valuable intermediates to achieve molecules with biological activity. 1 They can be obtained through photochemical transformation of pyridinium salts. 1,2 However, reaction in batch has low productivities. 3 Scale-up options are limited due to low penetration of photons in the solution with the increase of reactor dimensions. 4 By using flow reactors, we can overcome this problem, as we demonstrated in a previous work. 5 We hereby present the development of a new home-made UV reactor and a flow parallel quartz tube reactor to production intensification of 6-allyl