HuagongsheHuagongshe Chemistry Print Report · For research reference only
(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate → (1S,5R,6R,7R)-7-Benzoyloxy-6-[(E)-(4RS)-4-methyl-3-oxonon-1-en-6-inyl]-2-oxabicyclo[3,3,0]octan-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate | HCID 11000244 | — |
| Reactant | Dimethyl (3-methyl-2-oxooct-5-yn-1-yl)phosphonate | HCID 13269867 | — |
| Product | (1S,5R,6R,7R)-7-Benzoyloxy-6-[(E)-(4RS)-4-methyl-3-oxonon-1-en-6-inyl]-2-oxabicyclo[3,3,0]octan-3-one | HCID 13472481 | 90% |
Reaction Steps
Analogously to Example 1(g), 14.2 g of the title compound was synthesized from 9.85 g of 3-methyl-2-oxooct-5-inylphosphonic acid dimethyl ester and 11 g of (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3,3,0]octan-3-one [E. J. Corey et al., J. Amer. Chem. Soc. 91: 5675 (1969)].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04446147 |
| Source dataset | uspto-grants-1984_05 |
| ORD ID | ord-5f94b7bde36547ff8f57c187af699cf8 |
| Source note | uspto-grants-1984_05 |