Total synthesis of the latrunculins

AB Smith III, JW Leahy, I Noda…

Index: Journal of the American Chemical Society, , vol. 114, # 8 p. 2995 - 3007

Full Text: HTML

Citation Number: 59

Abstract

... Functionolly Interesting Compounds; Yoshida, Z., Ed.; Kodansha: Tokyo, 1986; Series in Organic Chemistry 25, pp ... 0002-7863/92/ 15 14-2995$03.00/0 0 1992 American Chemical Society ... of Rapport.15 However, the modest 39% yield for the latter process prompted us to devise ...

 Related Synthetic Route
N/A Structure

140146-97-0

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...

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N/A Structure

140146-99-2

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...

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(4R)-4-(3-hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxaspiro[4.5]decan-7-yl)butanoyl)-3-(4-methoxybenzyl)thiazolidin-2-one Structure

101860-56-4

(4R)-4-(3-hydro...

~%

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...

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(2R,3R)-3-hydroxybutan-2-yl (S)-4-((2R,4S,6R)-4,6-dihydroxy-6-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)tetrahydro-2H-pyran-2-yl)-2-methylbutanoate Structure

139944-42-6

(2R,3R)-3-hydro...

~%

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...

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N/A Structure

101915-87-1

N/A

~15%

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...

15-methoxy-Lat B Structure

105917-28-0

15-methoxy-Lat B

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(R)-4-((2R,4S,6R)-4-((tert-butyldimethylsilyl)oxy)-6-((S)-4-hydroxy-3-methylbutyl)-2-methoxytetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one Structure

139944-43-7

(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...

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N/A Structure

139944-35-7

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...

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(R)-4-((2R,4S,6R)-4-((tert-butyldimethylsilyl)oxy)-6-((S)-4-hydroxy-3-methylbutyl)-2-methoxytetrahydro-2H-pyran-2-yl)thiazolidin-2-one Structure

128359-72-8

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

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

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(S)-4-((2R,4S,6R)-4-((tert-butyldimethylsilyl)oxy)-6-methoxy-6-((R)-2-oxothiazolidin-4-yl)tetrahydro-2H-pyran-2-yl)-2-methylbutanal Structure

128359-73-9

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

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

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N/A Structure

128359-74-0

N/A

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

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(S,2Z,6E,8Z)-12-((2R,4S,6R)-4-hydroxy-6-methoxy-6-((R)-2-oxo-3-((2-(trimethylsilyl)ethoxy)carbonyl)thiazolidin-4-yl)tetrahydro-2H-pyran-2-yl)-3,10-dimethyldodeca-2,6,8-trienoic acid Structure

128359-79-5

(S,2Z,6E,8Z)-12...

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

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N/A Structure

128359-78-4

N/A

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

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N/A Structure

140146-97-0

N/A

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

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N/A Structure

140146-99-2

N/A

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

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(4R)-4-(3-hydroxy-4-((2R,3R,7R,10S)-2,3,10-trimethyl-1,4,6-trioxaspiro[4.5]decan-7-yl)butanoyl)-3-(4-methoxybenzyl)thiazolidin-2-one Structure

101860-56-4

(4R)-4-(3-hydro...

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

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(2R,3R)-3-hydroxybutan-2-yl (S)-4-((2R,4S,6R)-4,6-dihydroxy-6-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)tetrahydro-2H-pyran-2-yl)-2-methylbutanoate Structure

139944-42-6

(2R,3R)-3-hydro...

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

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(R)-4-((2R,4S,6R)-4-((tert-butyldimethylsilyl)oxy)-6-((S)-4-hydroxy-3-methylbutyl)-2-methoxytetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-one Structure

139944-43-7

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

~%

Latrunculin A Structure

76343-93-6

Latrunculin A

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