Milbemycin-avermectin studies. 5. Total synthesis of milbemycin. beta. 3 and its C (12) epimer

SR Schow, JD Bloom, AS Thompson…

Index: Schow,S.R.; Bloom,J.D.; Thompson,A.S. Journal of the American Chemical Society, 1986 , vol. 108, p. 2662

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Citation Number: 81

Abstract

Abstract: The total synthesis of milbemycin & (1) and its epimer, 12-epimilbemycin p3, is described. The central features of the synthetic strategy are (a) construction of the spiro ketal unit by nitrile oxide dipolar addition,(b) introduction of the requisite C (12) methyl center via a chelation-controlled cuprate addition in tandem with a stereocontrolled Ireland-Claisen rearrangement, and (c) construction of the southern hemisphere via a novel SN2'reaction ...

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Methanol Structure

67-56-1

Methanol

Methyl cyclopentenolone Structure

80-71-7

Methyl cyclopen...

~64%

2-Cyclopenten-1-one,2-methoxy-3-methyl- Structure

14189-85-6

2-Cyclopenten-1...

4-Methoxy-3-methylbenzoic acid Structure

6880-04-2

4-Methoxy-3-met...

~%

3-ethenyl-5-methoxy-3,6-dimethyl-isobenzofuran-1-one Structure

87503-68-2

3-ethenyl-5-met...

4-Methoxy-3-methylbenzaldehyde Structure

32723-67-4

4-Methoxy-3-met...

~%

3-ethenyl-5-methoxy-3,6-dimethyl-isobenzofuran-1-one Structure

87503-68-2

3-ethenyl-5-met...

Benzoyl chloride, 4-methoxy-3-methyl- (9CI) Structure

59931-48-5

Benzoyl chlorid...

~%

3-ethenyl-5-methoxy-3,6-dimethyl-isobenzofuran-1-one Structure

87503-68-2

3-ethenyl-5-met...

Ethanone,1-[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-5-methoxy-4-methylphenyl]- Structure

82045-52-1

Ethanone,1-[2-(...

~%

3-ethenyl-5-methoxy-3,6-dimethyl-isobenzofuran-1-one Structure

87503-68-2

3-ethenyl-5-met...

Oxazole,4,5-dihydro-2-(4-methoxy-3-methylphenyl)-4,4-dimethyl- Structure

82045-51-0

Oxazole,4,5-dih...

~%

3-ethenyl-5-methoxy-3,6-dimethyl-isobenzofuran-1-one Structure

87503-68-2

3-ethenyl-5-met...

N-(1-hydroxy-2-methylpropan-2-yl)-4-methoxy-3-methylbenzamide Structure

101472-02-0

N-(1-hydroxy-2-...

~%

3-ethenyl-5-methoxy-3,6-dimethyl-isobenzofuran-1-one Structure

87503-68-2

3-ethenyl-5-met...

N-(1-hydroxy-2-methylpropan-2-yl)-4-methoxy-3-methylbenzamide Structure

101472-02-0

N-(1-hydroxy-2-...

~%

Oxazole,4,5-dihydro-2-(4-methoxy-3-methylphenyl)-4,4-dimethyl- Structure

82045-51-0

Oxazole,4,5-dih...

4-Methoxy-3-methylbenzoic acid Structure

6880-04-2

4-Methoxy-3-met...

~%

Oxazole,4,5-dihydro-2-(4-methoxy-3-methylphenyl)-4,4-dimethyl- Structure

82045-51-0

Oxazole,4,5-dih...

4-Methoxy-3-methylbenzaldehyde Structure

32723-67-4

4-Methoxy-3-met...

~%

Oxazole,4,5-dihydro-2-(4-methoxy-3-methylphenyl)-4,4-dimethyl- Structure

82045-51-0

Oxazole,4,5-dih...

Benzoyl chloride, 4-methoxy-3-methyl- (9CI) Structure

59931-48-5

Benzoyl chlorid...

~%

Oxazole,4,5-dihydro-2-(4-methoxy-3-methylphenyl)-4,4-dimethyl- Structure

82045-51-0

Oxazole,4,5-dih...

Benzoyl chloride, 4-methoxy-3-methyl- (9CI) Structure

59931-48-5

Benzoyl chlorid...

~%

Ethanone,1-[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-5-methoxy-4-methylphenyl]- Structure

82045-52-1

Ethanone,1-[2-(...

N-(1-hydroxy-2-methylpropan-2-yl)-4-methoxy-3-methylbenzamide Structure

101472-02-0

N-(1-hydroxy-2-...

~%

Ethanone,1-[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-5-methoxy-4-methylphenyl]- Structure

82045-52-1

Ethanone,1-[2-(...

4-Methoxy-3-methylbenzaldehyde Structure

32723-67-4

4-Methoxy-3-met...

~%

Ethanone,1-[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-5-methoxy-4-methylphenyl]- Structure

82045-52-1

Ethanone,1-[2-(...


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