(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate → (1S,5R,6R,7R)-7-benzoyloxy-6-[(1E)-3-oxo-1-octen-5-ynyl]-2-oxabicyclo[3.3.0]octan-3-one

HRID 358357Notes

Reaction equation

HRID 358357 reaction equation
[CH:1]([C@H:3]1[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][C@H:8]2[C@@H:4]1[CH2:5][C:6](=[O:20])[O:7]2)=O.[O:21]=[C:22]([CH2:43][C:44]#[C:45][CH2:46][CH3:47])[CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:12]([O:11][C@@H:10]1[CH2:9][C@H:8]2[C@H:4]([CH2:5][C:6](=[O:20])[O:7]2)[C@H:3]1/[CH:1]=[CH:23]/[C:22](=[O:21])[CH2:43][C:44]#[C:45][CH2:46][CH3:47])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 11000244(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoateHCID 20448678HCID 20448678, compound

Product 1

HCID 70481263(1S,5R,6R,7R)-7-benzoyloxy-6-[(1E)-3-oxo-1-octen-5-ynyl]-2-oxabicyclo[3.3.0]octan-3-oneYield 98.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 7.4 g of (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (E. J. Corey et al., J. Chem. Soc., 91, 5675 (1969)) and 10.3 g of the phosphorane prepared in Example (23b) in 200 ml of absolute toluene is stirred at room temperature for 5.5 hours. The reaction solution is concentrated in vacuo and the residue is chromatographed over silica gel by gradient elution in hexane/40% ethyl acetate. 9.7 g of the title compound are obtained.

Workup

  1. concentrationThe reaction solution is concentrated in vacuo
  2. customthe residue is chromatographed over silica gel by gradient elution in hexane/40% ethyl acetate

Sources & evidence

ORD record
ord-a9a2d6feca93422588ebb0a6f20cc127
Source dataset
uspto-grants-1984_08
Patent number
US04466969

Reaction notes

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