Abstract
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/hydrogenation 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 alpha,beta-dioxygenated model aldehydes, which displayed similar anti-Felkin selectivities with organometallic nucleophiles.
Original language | English |
---|---|
Pages (from-to) | 1682-1694 |
Number of pages | 13 |
Journal | European Journal of Organic Chemistry |
Issue number | 9 |
DOIs | |
Publication status | Published - Mar 2011 |
MoE publication type | A1 Journal article-refereed |
Keywords
- Natural products
- Spiro compounds
- Anomeric effect
- Enantioselectivity
- Chirality
- FATTY-ACID ESTERS
- DIARRHETIC SHELLFISH TOXINS
- MUSSELS MYTILUS-EDULIS
- PART II
- STEREOCONTROLLED CYCLIZATION
- ALKOXIDE PRECOORDINATION
- CONVENIENT SYNTHESIS
- ASYMMETRIC SYNTHESES
- GREENSHELL MUSSELS
- DINOPHYSIS-ACUTA