acetogenins has been researched along with pyragonicin* in 3 studies
3 other study(ies) available for acetogenins and pyragonicin
| Article | Year |
|---|---|
Divergence en route to nonclassical annonaceous acetogenins. Synthesis of pyranicin and pyragonicin.
Syntheses of the nonclassical annonaceous acetogenins, pyranicin, and pyragonicin from common late-stage intermediates are presented. The construction of key elements relies on asymmetric HWE reactions, including the desymmetrization of a meso-dialdehyde and a parallel kinetic resolution of a racemic aldehyde. A stereoconvergent Pd-catalyzed substitution serves to install the C4 stereocenter in protected form with different orthogonal protective groups. A divergent strategy to form 1,4- and 1,6-diols, employing stereoselective Zn-mediated alkynylations, is used for completion of the core structures. Notably, the stereoselective coupling reaction toward pyragonicin proceeds with highly functionalized fragments. The methodology is further expanded by a divergent synthesis of all stereoisomers of the 2,3,6-trisubstituted tetrahydropyran subunit. Topics: 4-Butyrolactone; Acetogenins; Catalysis; Cyclization; Fatty Alcohols; Furans; Lactones; Platinum; Pyrans; Stereoisomerism | 2006 |
Synthesis of pyragonicin.
[structure: see text] A stereocontrolled convergent synthesis of the annonaceous acetogenin pyragonicin (1) is presented. The key intermediates were accessed using asymmetric Horner-Wadsworth-Emmons (HWE) methodology. A reagent controlled zinc-mediated stereoselective coupling, joining the two highly functionalized intermediates 3 and 4, then provided the core structure. Topics: Acetogenins; Annonaceae; Fatty Alcohols; Furans; Lactones; Molecular Structure; Stereoisomerism; Zinc | 2005 |
Total synthesis of the proposed structure for pyragonicin.
[structure: see text] The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SmI(2)-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation. Topics: Acetogenins; Annonaceae; Cyclization; Fatty Alcohols; Furans; Lactones; Molecular Structure; Stereoisomerism | 2005 |