Resolution of 7,7-dimethylbicyclo[3.2.0]hept-2-en-6-one using Mortierella ramanniana and 3α,20β-hydroxy-steroid dehydrogenase, photochemistry of 3-hydroxy-7,7-dimethylbicyclo[3.2.0]heptan-6-ones, and the synthesis of (+)-eldanolide
- 31 December 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 903-907
- https://doi.org/10.1039/p19870000903
Abstract
The fungus Mortierella ramanniana reduced 7,7-dimethylbicyclo[3.2.0]hept-2-en-6-one (1) to give the (6S)-endo-alcohol (9) and the (6S)-exo-alcohol (10). In contrast the enzyme 3α,20β-hydroxy-steroid dehydrogenase was found to give the (6S)-endo-alcohol (9) and recovered optically active ketone. Both processes produced the alcohol (9) in high optical purity. The (6S)-endo-alcohol (9) was converted into the lactone (+)-(4) a late stage synthon for the pheromone eldanolide (+)-(11).This publication has 3 references indexed in Scilit:
- A simple diastereoselective synthesis of (±)-eldanolideTetrahedron, 1986
- L'eldanolide, phéromone des glandes alaires de la pyrale de la canne à sucre, eldana saccharina (wlk.): structure et synthèse de ses deux énantiomèresTetrahedron, 1984
- Reduction of bicyclo [3.2.0] hept-2-en-6-one with dehydrogenase enzymes in whole cell preparations of some fungi and yeastsJournal of the Chemical Society, Perkin Transactions 1, 1983