Total Syntheses of the Actin??Binding Macrolides Latrunculin A, B, C, M, S and 16??epi??Latrunculin B

A Fürstner, D De Souza, L Turet…

Index: Chemistry - A European Journal, , vol. 13, # 1 p. 115 - 134

Full Text: HTML

Citation Number: 85

Abstract

... Chemistry – A European Journal: Previous article ... Latrunculin B: Although colonizing the densely populated coral reefs of the Red Sea, the sponge Negombata magnifica is conspicuously free from predation in its natural habitat due to an efficient chemical defense mechanism ...

 Related Synthetic Route
(3R,6S)-3-[tert-butyl(dimethyl)silyl]oxy-6-methylnon-7-ynal Structure

646994-44-7

(3R,6S)-3-[tert...

~%

2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)- Structure

76343-94-7

2-Thiazolidinon...

tert-butyldimethyl(((4R,7S)-7-methyldec-1-en-8-yn-4-yl)oxy)silane Structure

646994-43-6

tert-butyldimet...

~%

2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)- Structure

76343-94-7

2-Thiazolidinon...

(R)-3-(4-methoxybenzyl)-4-acetylthiazolidin-2-one Structure

101860-51-9

(R)-3-(4-methox...

~%

2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)- Structure

76343-94-7

2-Thiazolidinon...

N/A Structure

646994-49-2

N/A

~%

2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)- Structure

76343-94-7

2-Thiazolidinon...

(4R)-4-((5R,8S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-8-methylundec-9-ynoyl)-3-(4-methoxybenzyl)thiazolidin-2-one Structure

646994-46-9

(4R)-4-((5R,8S)...

~%

2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)- Structure

76343-94-7

2-Thiazolidinon...

N/A Structure

1053714-70-7

N/A

~%

2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)- Structure

76343-94-7

2-Thiazolidinon...

N/A Structure

646994-51-6

N/A

~%

2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)- Structure

76343-94-7

2-Thiazolidinon...

N/A Structure

928112-44-1

N/A

~%

2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)- Structure

76343-94-7

2-Thiazolidinon...

dimethyl 2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-2-oxoethyl-phosphonate Structure

861821-43-4

dimethyl 2-((R)...

~%

2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)- Structure

76343-94-7

2-Thiazolidinon...

N/A Structure

861821-42-3

N/A

~%

2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)- Structure

76343-94-7

2-Thiazolidinon...

(R)-4-((2R,4S,6R)-2,4-dihydroxy-6-((S)-3-methylhex-4-yn-1-yl)tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one Structure

646994-48-1

(R)-4-((2R,4S,6...

~%

2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)- Structure

76343-94-7

2-Thiazolidinon...

N/A Structure

128359-80-8

N/A

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

(2R,4R,6R)-2-methoxy-6-((S)-3-methylhex-4-yn-1-yl)-2-((R)-2-oxothiazolidin-4-yl)tetrahydro-2H-pyran-4-yl (2Z,6E)-3-methyldeca-2,6-dien-8-ynoate Structure

861821-51-4

(2R,4R,6R)-2-me...

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

Structure

861821-53-6

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

(2R,4R,6R)-2-methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-((S)-3-methylhex-4-yn-1-yl)tetrahydro-2H-pyran-4-yl (2Z,6E)-3-methyldeca-2,6-dien-8-ynoate Structure

861821-49-0

(2R,4R,6R)-2-me...

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

2-(trimethylsilyl)ethyl (R)-4-((2R,4R,6R)-2-methoxy-4-(((2Z,6E)-3-methyldeca-2,6-dien-8-ynoyl)oxy)-6-((S)-3-methylhex-4-yn-1-yl)tetrahydro-2H-pyran-2-yl)-2-oxothiazolidine-3-carboxylate Structure

861821-52-5

2-(trimethylsil...

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

N/A Structure

646994-49-2

N/A

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

N/A Structure

1053714-70-7

N/A

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

(3R,6S)-3-[tert-butyl(dimethyl)silyl]oxy-6-methylnon-7-ynal Structure

646994-44-7

(3R,6S)-3-[tert...

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

tert-butyldimethyl(((4R,7S)-7-methyldec-1-en-8-yn-4-yl)oxy)silane Structure

646994-43-6

tert-butyldimet...

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

dimethyl 2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-2-oxoethyl-phosphonate Structure

861821-43-4

dimethyl 2-((R)...

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

N/A Structure

861821-42-3

N/A

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

(R)-4-((2R,4S,6R)-2,4-dihydroxy-6-((S)-3-methylhex-4-yn-1-yl)tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one Structure

646994-48-1

(R)-4-((2R,4S,6...

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

(R)-3-(4-methoxybenzyl)-4-acetylthiazolidin-2-one Structure

101860-51-9

(R)-3-(4-methox...

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

(4R)-4-((5R,8S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-8-methylundec-9-ynoyl)-3-(4-methoxybenzyl)thiazolidin-2-one Structure

646994-46-9

(4R)-4-((5R,8S)...

~%

Latrunculin A Structure

76343-93-6

Latrunculin A


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