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US 6,605,726 B1Granted
Method for producing epothilone B and derivatives, and intermediate products for this method
AssigneeSchering Corporation
InventorsJohann Mulzer, Andreas Mantoulidis, Elisabeth Öhler
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Abstract
The invention relates to a method for producing epothilone B and derivatives, and to intermediate products for this method. According to the novel method, the epothilone B or derivatives are produced in high yields from the C1-C6, C7-C10 and C11-C20-fragments 2, 3 and 4 that can be obtained economically and diastereomerically purely (the variable radicals having the meanings given in the description ).
Claims18
A process for production of a compound of formula I:
- wherein
- R is methyl, and
- R6 is a straight-chain or branched-chain alkyl group with up to 6 carbon atoms, a cycloalkylalkyl group with up to 10 carbon atoms, a phenyl group, 1- or 2-naphthyl group, a heteroaryl group, benzyl, or a methylheteroaryl group,
- said process comprising:
- a) reacting a compound of formula 3
- wherein
- PG3 is a hydroxy protective group, and
- FG3 is a phenylsulfonyl group,
- with a compound of formula 4
- wherein
- FG4 is an iodine atom or another leaving group, and
- PG4 is a hydroxy protective group,
- to form a compound of formula 34-I
- b) reacting the compound of formula 34-I with a compound of formula 2
- wherein
- PG21 and PG22, independently of one another, are in each case a hydroxy protective group,
- to form a compound of formula 234
- c) reacting the compound of formula 234 over the following stages
- d) converting the resultant compound by epoxidation to form a compound according to formula I.
16 more elements
A process comprising:
- a) reacting a compound of formula 3
- wherein
- PG3 is a hydroxy protective group, and
- FG3 is a phenylsulfonyl group,
- with a compound of formula 4
- wherein
- FG4 is an iodine atom or another leaving group, and
- PG4 is a hydroxy protective group,
- to form a compound of formula 34-I
- b) reacting the compound of formula 34-I with a compound of formula 2
- wherein
- PG21 and PG22, independently of one another, are in each case a hydroxy protective group, and
- R6 is a straight-chain or branched-chain alkyl group with up to 6 carbon atoms, a cycloalkylalkyl group with up to 10 carbon atoms, a phenyl group, 1- or 2-naphthyl group, a heteroaryl group, benzyl, or a methylheteroaryl group, to form a compound of formula 234
- c) reacting the compound of formula 234 over the following stages
11 more elements
Dependencies are inferred from the claim text.