Total Synthesis of Pyranicin
- 22 December 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (2) , 199-202
- https://doi.org/10.1021/ol0479242
Abstract
A stereocontrolled convergent synthesis of the annonaceous acetogenin pyranicin (1) is presented. Asymmetric Horner−Wadsworth−Emmons (HWE) reactions were used to access key intermediates. The tetrahydropyran derivative 2 was obtained via an asymmetric desymmetrization of the meso-dialdehyde 6, and the butenolide fragment was constructed using a stereoconvergent reaction sequence involving a parallel kinetic HWE resolution followed by a Pd-catalyzed allylic substitution. The C10/C15 1,6-diol motif was installed using Carreira's asymmetric acetylide addition methodology.Keywords
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