(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-7-inyl]-2-oxabicyclo[3,3,0]octan-3-one

HRID 543519

反応式

HRID 543519 の反応式
COP([CH2:7][C:8](=[O:16])[CH:9]([CH3:15])[CH2:10][CH2:11][C:12]#[C:13][CH3:14])(=O)OC.[CH:17]([C@H:19]1[C@H:26]([O:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:25][C@H:24]2[C@@H:20]1[CH2:21][C:22](=[O:36])[O:23]2)=O>>[C:28]([O:27][C@@H:26]1[CH2:25][C@H:24]2[C@H:20]([CH2:21][C:22](=[O:36])[O:23]2)[C@H:19]1/[CH:17]=[CH:7]/[C:8](=[O:16])[CH:9]([CH3:15])[CH2:10][CH2:11][C:12]#[C:13][CH3:14])(=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

参加物

3

反応物 2

HCID 11000244(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoateHCID 538600643-Methyl-2-oxooct-6-inylphosphonic acid dimethyl ester

生成物 1

HCID 18650099(1S,5R,6R,7R)-7-Benzoyloxy-6-[(E)-(4RS) 4-methyl-3-oxonon-1-en-7-inyl]-2-oxabicyclo[3,3,0]octan-3-one収率 85.8%

実験手順

Analogously to Example 1(g), 7.4 g of the title compound was synthesized from 5.4 g of 3-methyl-2-oxooct-6-inylphosphonic acid dimethyl ester and 6 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)].

出典と根拠

ORDレコード
ord-463b5e102a7545b3bc5e852423f7c37e
出典データセット
uspto-grants-1984_05
特許番号
US04446147

関連ノート

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