Abstract: In this lecture, I would like to present efficient synthetic routes towards the total synthesis of syringolide 1 (2)^1,2 and secosyrin 1 (3),¹ employing 2,4-disubstituted furan 1 as a common precursor. A modified total synthesis of prehispanolone (6)³ from (S)-(+)-Wieland-Miescher ketone (4) via hispanolone (5) will also be discussed. Our methodology for the synthesis of 3,4-disubstituted-lH-pyrroles⁴ and for the generation of 3,4-didehydrothiophene⁵ has also guided us to the successful identification of 1-tert-butoxycarbonyl-3,4-didehydro-1H-pyrrole (7),which is presumably the most strained heterocyclic cumulene ever recorded.