(E)-2-(3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-one → 3,3a,4,5,6,6a-hexahydro-2H-pentalen-1-one

HRID 462803Notes

Reaction equation

HRID 462803 reaction equation
[Si](OC(COC1C=CC=CC=1)/C=C/[CH:12]1[CH2:19][CH2:18][CH:17]2[CH:13]1[CH2:14][CH2:15][C:16]2=[O:20])(C(C)(C)C)(C)C.OC(C1CC2C(CCC2)C1=O)CCCC(OC)=O>>[CH:13]12[CH2:14][CH2:15][C:16](=[O:20])[CH:17]1[CH2:18][CH2:19][CH2:12]2

Participants

3

Reactant 2

HCID 20397195(E)-2-(3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-oneHCID 867401063-(1-Hydroxy-methoxycarbonylbut-1-yl)bicyclo[3,3,0]octan-2-one

Product 1

HCID 1406313,3a,4,5,6,6a-hexahydro-2H-pentalen-1-one

Procedure

By proceeding in a manner to that described in Reference Example 47, but replacing the starting material by the appropriate quantity of (E)-2-(3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl)bicyclo[3,3,0]octan-6-one, prepared as described in Reference Example 52, and in the form of (±)-(E)-2β-[(mixture of 3α and 3β)-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl]bicyclo[3,3,0]octan-6-one, there was prepared 6-(E)-3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl-3-(1-hydroxy-4-methoxycarbonylbut-1-yl)-bicyclo[3,3,0]octan-2-one, in the form of (±)-6β-[(E)-(mixture of 3α and 3β)-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl]-3-(1-hydroxy-4-methoxycarbonylbut-1-yl)bicyclo[3,3,0]octan-2-one.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-db690595857644a3a1c592e7211d1c31
Source dataset
uspto-grants-1985_05
Patent number
US04517202

Reaction notes

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