6533b86dfe1ef96bd12ca233
RESEARCH PRODUCT
Synthetic Studies towards Pectenotoxin-2: Synthesis of the Nonanomeric 10-epi-ABCDE Ring Segment by Kinetic Spiroketalization
Petri M. PihkoA. PiisolaK. Syam KrishnanJatta E. Ahosubject
chemistry.chemical_classificationAddition reactionStereochemistryOrganic ChemistryRing (chemistry)MetathesisAldehydeChemical synthesischemistryNucleophilePhysical and Theoretical ChemistryChirality (chemistry)ta116Lactonedescription
The synthesis of the nonanomeric 10-epi-ABCDE ring system of pectenotoxin-2 has been achieved by using a kinetic spiroketalization reaction. The synthesis of the spiroketalization precursor was achieved through a cross-metathesis/hydro-genation sequence. The formation of the epi-C10 isomer resulted from an unexpected anti-Felkin selective addition of organometallic nucleophiles to the advanced CDE ring precursor. This addition reaction was investigated with differently protected α,β-dioxygenated model aldehydes, which displayed similar anti-Felkin selectivities with organometallic nucleophiles.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-02-14 | European Journal of Organic Chemistry |