A synthesis of (+)-decarestrictine L 1, a cholesterol biosynthesis inhibitory metabolite isolated from Penicillium simplicissimum, is described. Beginning from tri-O-acetyl- -glucal, alkylation with trimethylaluminum introduced the axial methyl group at C-2 in a stereoselective fashion. Chain extension at the C-6 carbon was accomplished by generation of the primary tosylate, followed by displacement with cyanide anion. The synthesis of (+)-1 was completed in 13 steps and 6.3% overall yield.
Lukesh, Julie and Donaldson, William, "Synthesis of (+)-decarestrictine L" (2003). Chemistry Faculty Research and Publications. 65.
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Accepted version. Tetrahedron: Asymmetry, Vol. 14, Issue 6 (2003), pp 757-762. DOI: 10.1016/S0957-4166(03)00126-5. © 2003 Elsevier. Used with permission.