6-[(E)-3-tert-Butyldimethylsilyloxy-4-phenoxybut-1-enyl]-3-[(E)-4-methoxycarbonylbutylidene]bicyclo[3,3,0]octan-2-one → 3-(1-Hydroxy-methoxycarbonylbut-1-yl)bicyclo[3,3,0]octan-2-one

HRID 462804Notes

Reaction equation

HRID 462804 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][CH:15]([CH:21]([OH:29])[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:16]2=[O:20])(C(C)(C)C)(C)C.[Si](OC(COC1C=CC=CC=1)/C=C/C1CCC2C1C/C(=C\CCCC(OC)=O)/C2=O)(C(C)(C)C)(C)C.COC(CCC/C=C1/C(=O)C2C(C/1)CCC2)=O>>[OH:29][CH:21]([CH:15]1[CH2:14][CH:13]2[CH:17]([CH2:18][CH2:19][CH2:12]2)[C:16]1=[O:20])[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]

Participants

4

Reactant 3

HCID 203971906-[(E)-3-tert-Butyldimethylsilyloxy-4-phenoxybut-1-enyl]-3-[(E)-4-methoxycarbonylbutylidene]bicyclo[3,3,0]octan-2-oneHCID 203972146-[(E)-3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl]-3-(1-hydroxy-4-methoxycarbonylbut-1-yl)bicyclo[3,3,0]octan-2-oneHCID 867400973-[(E)-4-methoxycarbonylbutylidene]bicyclo[3,3,0]octan-2-one

Product 1

HCID 867401063-(1-Hydroxy-methoxycarbonylbut-1-yl)bicyclo[3,3,0]octan-2-one

Procedure

By proceeding in a manner similar to that described in Reference Example 48, but replacing the starting material by the appropriate quantity of 6-[(E)-3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl]-3-(1-hydroxy-4-methoxycarbonylbut-1-yl)bicyclo[3,3,0]octan-2-one, prepared as described in Reference Example 53, and in the form of (±)-6β-[(E)-(mixture of 3α and 3β)-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl]-3-(1-hydroxy-methoxycarbonylbut-1-yl)bicyclo[3,3,0]octan-2-one, there was prepared 6-[(E)-3-tert-butyldimethylsilyloxy-4-phenoxybut-1-enyl]-3-[(E)-4-methoxycarbonylbutylidene]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-[(E)-4-methoxycarbonylbutylidene]bicyclo[3,3,0]octan-2-one, otherwise known as (±)-methyl (5E,13E)-(9S), [mixture of (15R) and (15S)]-6a-oxo-6,9-methano-15-tert-butyldimethylsilyloxy-16-phenoxy-17,18,19,20-tetranorprosta-5,13-dienoate.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-e5cf6e87bace468dae3e531d4da2089d
Source dataset
uspto-grants-1985_05
Patent number
US04517202

Reaction notes

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