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Published on: March 6, 2019
Synthesis of Squamostanal-A
H Konno1, H Makabe1, A Tanaka1,2
1a Department of Applied Biological Chemistry, Faculty of Agriculture , Graduate School of Agriculture, Tohoku University, 1-1 Tsutsumidori Amamiyamachi , Aoba-ku, Sendai 981 , Japan.
Abstract:
The first synthesis of squamostanal-A (1), separated as a degradation product of tetrahydrofuranic acetogenins, is described. Iodide 7, which corresponds to the latent aldehyde moiety of 1, was prepared through a 2-step sequence from 13-[tetrahydropyran-2'- yloxy]-2-tridecyn-l-ol (5). The NaHMDS-based coupling reaction of 7 with γ-lactone 8 gave compound 9, which by a 3-step sequence, was coverted to 1.
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