82031-74-1Relevant articles and documents
Propene as an Atom-Economical Linchpin for Concise Total Synthesis of Polyenes: Piericidin A
Trost, Barry M.,Gholami, Hadi
supporting information, p. 11623 - 11626 (2018/09/21)
A concise and convergent total synthesis of piericidin A is disclosed. The synthesis hinges on the utilization of propene as a synthetic linchpin to merge the properly elaborated alkyne fragments, leading to the 1,3,6-triene motif of piericidin A. Utilization of propene as a unique alkene, capable of sequential coupling with two alkynes, is further illustrated in the context of various 1,3,6-triene products. The latter process proceeds with high atom economy and efficiently gives rise to complex frameworks from readily accessible alkyne substrates. This strategic C-C bond formation offers an orthogonal paradigm in the design of synthetic routes, leading to higher step economy and more efficient syntheses of polyunsaturated natural products.
Vinyl Cations, 37. Rearrangement of Cyclic Homopropargyl Sulfonates to Condensed Cyclobutanones and Cyclopropyl Ketones
Hanack, Michael,Schuhmacher, Werner,Kunzmann, Erich
, p. 1467 - 1487 (2007/10/02)
Cyclic homopropargyl sulfonates 8 (tosylates, triflates, nonaflates, and damsylates) are prepared and solvolysed.The resulting rearrangement reactions are studied with respect to the properties of the solvents used, leaving groups, the substituent on the triple bond, and with respect to the ring size of the sulfonates 8.
