Synthesis of (+)-decarestrictine L

Authors

Julie Lukesh, Marquette UniversityFollow
William Donaldson, Marquette UniversityFollow

Document Type

Article

Publication Date

3-2003

Publisher

Elsevier

Source Publication

Tetrahedron: Asymmetry

Source ISSN

0957-4166

Abstract

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.

Comments

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.

Recommended Citation

Lukesh, Julie and Donaldson, William, "Synthesis of (+)-decarestrictine L" (2003). Chemistry Faculty Research and Publications. 65.
https://epublications.marquette.edu/chem_fac/65