The prefix seco in tetrapyrrole nomenclature signifies that the macrocyclic ring of a porphyrin, chlorophyll, or corrin is opened at the specified position to the corresponding acyclic (linear) tetrapyrrole. This nomenclature reflects chemical reactions involving respective ring openings and ring closures.
Seco-tetrapyrroles as products of biological and chemical degradation Linear tetrapyrroles originating from natural chlorophyll breakdown during plant senescence, known only since the 1990s, were first named as 4,5-seco-phytoporphyrins, since about 2014 as phyllobilins, with this systematic name expressing their origin from chlorophyll and their structural relation to bile pigments (fig. 1). Chemical ring cleavage of cyclic tetrapyrroles also produces seco-derivatives, as in the photooxygenolysis of vitamin B12 (fig. 2).
Seco-corrins in corrin syntheses In the Harvard (Woodward)/ETH (Eschenmoser) variant of the two total syntheses of vitamin B12, the corrin macrocyle is built by coupling an A/D- (Harvard) and a B/C (ETH) component, first at meso-C-15 between rings D and C, followed by ring closure of the resulting seco-corrin at C-5, using the Eschenmoser sulfide contraction developed at ETH for both coupling reactions (fig. 3).
In the photochemical ETH variant of these total syntheses, the corrin ring is closed directly between rings A and D – as typical for corrins, meso position C20 missing – in an A/D-seco-corrin → corrin cycloisomerization (fig. 4). Other corrins were synthesized by Eschenmoser et al. from seco-corrins by A/B ring closure via imidoester–enamine C–C condensation, sulfide contraction, or by photochemical A/D cyclization.
References

![Seco (tetrapyrrole): Figure 2. Photooxygenolysis of cobester and vitamin B12 to 5,6- and 14,15-seco-corrins[5][6]](https://upload.wikimedia.org/wikipedia/commons/thumb/f/f6/PhotoOx_B12.png/500px-PhotoOx_B12.png?utm_source=en.wikipedia.org&utm_campaign=parser&utm_content=thumbnail)


