The Journal of Organic Chemistry

Stereoselective total synthesis of the antitumor antibiotic (-)-bactobolin

RS Garigipati, SM Weinreb

Index: Garigipati, Ravi S.; Weinreb, Steven M. Journal of Organic Chemistry, 1988 ,  vol. 53,  # 17  p. 4143 - 4145

Full Text: HTML

Citation Number: 19

Abstract

Acknowledgment. We appreciate the financial support provided by the National Institutes of Health (Grant GM 28663), Eli Lilly and Company, and the Alfred P. Sloan Foundation. High-field (360 MHz) 'H NMR and NMR spectra were obtained on a spectrometer purchased with funds provided, in part, by the National Science Foun- dation (Grant CHE-80-24328). Mass spectra were obtained through the National Science Foundation Regional Mass Spectroscopy ...

 Related Synthetic Route
endo-(+/-)-N-(3-oxo-2-oxabicyclo[3.3.1]non-6-en-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-35-5

endo-(+/-)-N-(3...

~%

N-[1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-oxopropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-39-9

N-[1-(hexahydro...

N-((1R,6R,9R)-8-oxo-3,7-dioxatricyclo[4.3.1.02,4]decan-9-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-36-6

N-((1R,6R,9R)-8...

~%

N-[1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-oxopropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-39-9

N-[1-(hexahydro...

N-((1S,4S,5S,6S,7S)-6,7-dihydroxy-3-oxo-2-oxabicyclo[3.3.1]nonan-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-37-7

N-((1S,4S,5S,6S...

~%

N-[1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-oxopropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-39-9

N-[1-(hexahydro...

(S)-2-((3aS,4S,6S,7aS)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-4-yl)-N-methoxy-N-methyl-2-(2-(trimethylsilyl)ethylsulfonamido)acetamide Structure

126423-76-5

(S)-2-((3aS,4S,...

~%

N-[1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-oxopropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-39-9

N-[1-(hexahydro...

endo-(+/-)-N-(3-oxo-2-oxabicyclo[3.3.1]non-6-en-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-35-5

endo-(+/-)-N-(3...

~%

N-((1S,4S,5S,6S,7S)-6,7-dihydroxy-3-oxo-2-oxabicyclo[3.3.1]nonan-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-37-7

N-((1S,4S,5S,6S...

endo-(+/-)-N-(3-oxo-2-oxabicyclo[3.3.1]non-6-en-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-35-5

endo-(+/-)-N-(3...

~98%

N-((1R,6R,9R)-8-oxo-3,7-dioxatricyclo[4.3.1.02,4]decan-9-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-36-6

N-((1R,6R,9R)-8...

endo-(+/-)-N-(3-oxo-2-oxabicyclo[3.3.1]non-6-en-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-35-5

endo-(+/-)-N-(3...

~%

(S)-2-((3aS,4S,6S,7aS)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-4-yl)-N-methoxy-N-methyl-2-(2-(trimethylsilyl)ethylsulfonamido)acetamide Structure

126423-76-5

(S)-2-((3aS,4S,...

N-((1R,6R,9R)-8-oxo-3,7-dioxatricyclo[4.3.1.02,4]decan-9-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-36-6

N-((1R,6R,9R)-8...

~%

(S)-2-((3aS,4S,6S,7aS)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-4-yl)-N-methoxy-N-methyl-2-(2-(trimethylsilyl)ethylsulfonamido)acetamide Structure

126423-76-5

(S)-2-((3aS,4S,...

N-((1S,4S,5S,6S,7S)-6,7-dihydroxy-3-oxo-2-oxabicyclo[3.3.1]nonan-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-37-7

N-((1S,4S,5S,6S...

~%

(S)-2-((3aS,4S,6S,7aS)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-4-yl)-N-methoxy-N-methyl-2-(2-(trimethylsilyl)ethylsulfonamido)acetamide Structure

126423-76-5

(S)-2-((3aS,4S,...

endo-(+/-)-N-(3-oxo-2-oxabicyclo[3.3.1]non-6-en-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-35-5

endo-(+/-)-N-(3...

~%

N-[8-(dichloromethyl)-3a,4,8,9,9a,9b-hexahydro-5-hydroxy-2,2,8-trimethyl-6H-1,3-dioxolo[4,5-f][2]benzopyran-9-yl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-43-5

N-[8-(dichlorom...

N-((1R,6R,9R)-8-oxo-3,7-dioxatricyclo[4.3.1.02,4]decan-9-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-36-6

N-((1R,6R,9R)-8...

~%

N-[8-(dichloromethyl)-3a,4,8,9,9a,9b-hexahydro-5-hydroxy-2,2,8-trimethyl-6H-1,3-dioxolo[4,5-f][2]benzopyran-9-yl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-43-5

N-[8-(dichlorom...

N-((1S,4S,5S,6S,7S)-6,7-dihydroxy-3-oxo-2-oxabicyclo[3.3.1]nonan-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-37-7

N-((1S,4S,5S,6S...

~%

N-[8-(dichloromethyl)-3a,4,8,9,9a,9b-hexahydro-5-hydroxy-2,2,8-trimethyl-6H-1,3-dioxolo[4,5-f][2]benzopyran-9-yl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-43-5

N-[8-(dichlorom...

N-[1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-oxopropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-39-9

N-[1-(hexahydro...

~%

N-[8-(dichloromethyl)-3a,4,8,9,9a,9b-hexahydro-5-hydroxy-2,2,8-trimethyl-6H-1,3-dioxolo[4,5-f][2]benzopyran-9-yl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-43-5

N-[8-(dichlorom...

N-[3,3-dichloro-1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-hydroxy-2-methylpropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-40-2

N-[3,3-dichloro...

~%

N-[8-(dichloromethyl)-3a,4,8,9,9a,9b-hexahydro-5-hydroxy-2,2,8-trimethyl-6H-1,3-dioxolo[4,5-f][2]benzopyran-9-yl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-43-5

N-[8-(dichlorom...

(S)-2-((3aS,4S,6S,7aS)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-4-yl)-N-methoxy-N-methyl-2-(2-(trimethylsilyl)ethylsulfonamido)acetamide Structure

126423-76-5

(S)-2-((3aS,4S,...

~%

N-[8-(dichloromethyl)-3a,4,8,9,9a,9b-hexahydro-5-hydroxy-2,2,8-trimethyl-6H-1,3-dioxolo[4,5-f][2]benzopyran-9-yl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-43-5

N-[8-(dichlorom...

endo-(+/-)-N-(3-oxo-2-oxabicyclo[3.3.1]non-6-en-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-35-5

endo-(+/-)-N-(3...

~%

N-[3,3-dichloro-1-(hexahydro-2,2-dimethyl-6-oxo-1,3-benzodioxol-4-yl)-2-methylpropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-41-3

N-[3,3-dichloro...

N-((1R,6R,9R)-8-oxo-3,7-dioxatricyclo[4.3.1.02,4]decan-9-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-36-6

N-((1R,6R,9R)-8...

~%

N-[3,3-dichloro-1-(hexahydro-2,2-dimethyl-6-oxo-1,3-benzodioxol-4-yl)-2-methylpropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-41-3

N-[3,3-dichloro...

N-((1S,4S,5S,6S,7S)-6,7-dihydroxy-3-oxo-2-oxabicyclo[3.3.1]nonan-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-37-7

N-((1S,4S,5S,6S...

~%

N-[3,3-dichloro-1-(hexahydro-2,2-dimethyl-6-oxo-1,3-benzodioxol-4-yl)-2-methylpropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-41-3

N-[3,3-dichloro...

N-[1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-oxopropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-39-9

N-[1-(hexahydro...

~%

N-[3,3-dichloro-1-(hexahydro-2,2-dimethyl-6-oxo-1,3-benzodioxol-4-yl)-2-methylpropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-41-3

N-[3,3-dichloro...

(S)-2-((3aS,4S,6S,7aS)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-4-yl)-N-methoxy-N-methyl-2-(2-(trimethylsilyl)ethylsulfonamido)acetamide Structure

126423-76-5

(S)-2-((3aS,4S,...

~%

N-[3,3-dichloro-1-(hexahydro-2,2-dimethyl-6-oxo-1,3-benzodioxol-4-yl)-2-methylpropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-41-3

N-[3,3-dichloro...

endo-(+/-)-N-(3-oxo-2-oxabicyclo[3.3.1]non-6-en-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-35-5

endo-(+/-)-N-(3...

~%

N-[3,3-dichloro-1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-hydroxy-2-methylpropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-40-2

N-[3,3-dichloro...

N-((1R,6R,9R)-8-oxo-3,7-dioxatricyclo[4.3.1.02,4]decan-9-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-36-6

N-((1R,6R,9R)-8...

~%

N-[3,3-dichloro-1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-hydroxy-2-methylpropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-40-2

N-[3,3-dichloro...

N-((1S,4S,5S,6S,7S)-6,7-dihydroxy-3-oxo-2-oxabicyclo[3.3.1]nonan-4-yl)-2-(trimethylsilyl)ethanesulfonamide Structure

115534-37-7

N-((1S,4S,5S,6S...

~%

N-[3,3-dichloro-1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-hydroxy-2-methylpropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-40-2

N-[3,3-dichloro...

(S)-2-((3aS,4S,6S,7aS)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-4-yl)-N-methoxy-N-methyl-2-(2-(trimethylsilyl)ethylsulfonamido)acetamide Structure

126423-76-5

(S)-2-((3aS,4S,...

~%

N-[3,3-dichloro-1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-hydroxy-2-methylpropyl]-2-(trimethylsilyl)ethanesulfonamide Structure

115534-40-2

N-[3,3-dichloro...


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