Total syntheses of fungal metabolites and functionalized furanones

KM Chen, JE Semple, MM Joullie

Index: Chen, Kau-Ming; Semple, J. Edward; Joullie, Madeleine M. Journal of Organic Chemistry, 1985 , vol. 50, # 21 p. 3997 - 4005

Full Text: HTML

Citation Number: 30

Abstract

Simple, efficient syntheses of the fungal metabolites colletochlorin D and (f)-ascofuranone and one of its stereoisomers are described. Our investigations of functionalized furanones also enabled us to develop a nine-step (22% overall yield) synthesis of geiparvarin, a natural product isolated from the leaves of Geigera paruiflora Lindl.

 Related Synthetic Route
Geraniol Structure

106-24-1

Geraniol

Benzyl bromide Structure

100-39-0

Benzyl bromide

~90%

3,7-dimethylocta-2,6-dienoxymethylbenzene Structure

52188-73-5

3,7-dimethyloct...

N/A Structure

93741-07-2

N/A

~70%

5-chloro-3-[(2E,6E)-7-(5,5-dimethyl-4-oxooxolan-2-yl)-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde Structure

86832-77-1

5-chloro-3-[(2E...

(+/-)-(2E,6E)-7-(3',3'-dimethyl-4',4'-ethylenedioxy-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadien-1-ol Structure

86771-43-9

(+/-)-(2E,6E)-7...

~%

5-chloro-3-[(2E,6E)-7-(5,5-dimethyl-4-oxooxolan-2-yl)-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde Structure

86832-77-1

5-chloro-3-[(2E...

(+/-)-(2E,6E)-7-(3',3'-dimethyl-4',4'-ethylenedioxy-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl bromide Structure

86771-44-0

(+/-)-(2E,6E)-7...

~%

5-chloro-3-[(2E,6E)-7-(5,5-dimethyl-4-oxooxolan-2-yl)-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde Structure

86832-77-1

5-chloro-3-[(2E...

3-chloro-4,6-dihydroxy-2-methylbenzaldehyde Structure

83324-59-8

3-chloro-4,6-di...

~%

5-chloro-3-[(2E,6E)-7-(5,5-dimethyl-4-oxooxolan-2-yl)-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde Structure

86832-77-1

5-chloro-3-[(2E...

N/A Structure

93741-03-8

N/A

~%

5-chloro-3-[(2E,6E)-7-(5,5-dimethyl-4-oxooxolan-2-yl)-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde Structure

86832-77-1

5-chloro-3-[(2E...

N/A Structure

93741-04-9

N/A

~%

5-chloro-3-[(2E,6E)-7-(5,5-dimethyl-4-oxooxolan-2-yl)-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde Structure

86832-77-1

5-chloro-3-[(2E...

N/A Structure

93741-05-0

N/A

~%

5-chloro-3-[(2E,6E)-7-(5,5-dimethyl-4-oxooxolan-2-yl)-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde Structure

86832-77-1

5-chloro-3-[(2E...

3-(6,6-dimethyl-1,4,7-trioxaspiro[4.4]nonan-8-yl)but-2-en-1-ol Structure

93741-02-7

3-(6,6-dimethyl...

~%

5-chloro-3-[(2E,6E)-7-(5,5-dimethyl-4-oxooxolan-2-yl)-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde Structure

86832-77-1

5-chloro-3-[(2E...

N/A Structure

93741-06-1

N/A

~%

5-chloro-3-[(2E,6E)-7-(5,5-dimethyl-4-oxooxolan-2-yl)-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde Structure

86832-77-1

5-chloro-3-[(2E...

Orcinol Structure

504-15-4

Orcinol

~%

5-chloro-3-[(2E,6E)-7-(5,5-dimethyl-4-oxooxolan-2-yl)-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde Structure

86832-77-1

5-chloro-3-[(2E...

2,4-Dihydroxy-6-methylbenzaldehyde Structure

487-69-4

2,4-Dihydroxy-6...

~%

5-chloro-3-[(2E,6E)-7-(5,5-dimethyl-4-oxooxolan-2-yl)-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde Structure

86832-77-1

5-chloro-3-[(2E...

N/A Structure

89983-26-6

N/A

~%

5-chloro-3-[(2E,6E)-7-(5,5-dimethyl-4-oxooxolan-2-yl)-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde Structure

86832-77-1

5-chloro-3-[(2E...

7-[(E)-3-(5,5-dimethyl-4-oxooxolan-2-yl)but-2-enoxy]chromen-2-one Structure

98066-12-7

7-[(E)-3-(5,5-d...

~74%

2H-1-Benzopyran-2-one,7-[[(2E)-3-(4,5-dihydro-5,5-dimethyl-4-oxo-2-furanyl)-2-buten-1-yl]oxy]- Structure

36413-91-9

2H-1-Benzopyran...

N/A Structure

93741-03-8

N/A

~%

2H-1-Benzopyran-2-one,7-[[(2E)-3-(4,5-dihydro-5,5-dimethyl-4-oxo-2-furanyl)-2-buten-1-yl]oxy]- Structure

36413-91-9

2H-1-Benzopyran...

N/A Structure

89983-26-6

N/A

~98%

3-(6,6-dimethyl-1,4,7-trioxaspiro[4.4]nonan-8-yl)but-2-en-1-ol Structure

93741-02-7

3-(6,6-dimethyl...

7-Hydroxycoumarine Structure

93-35-6

7-Hydroxycoumarine

~%

7-[(E)-3-(5,5-dimethyl-4-oxooxolan-2-yl)but-2-enoxy]chromen-2-one Structure

98066-12-7

7-[(E)-3-(5,5-d...

3-(6,6-dimethyl-1,4,7-trioxaspiro[4.4]nonan-8-yl)but-2-en-1-ol Structure

93741-02-7

3-(6,6-dimethyl...

~%

7-[(E)-3-(5,5-dimethyl-4-oxooxolan-2-yl)but-2-enoxy]chromen-2-one Structure

98066-12-7

7-[(E)-3-(5,5-d...

N/A Structure

89983-26-6

N/A

~%

7-[(E)-3-(5,5-dimethyl-4-oxooxolan-2-yl)but-2-enoxy]chromen-2-one Structure

98066-12-7

7-[(E)-3-(5,5-d...

(+/-)-(E)-8-(3-chloro-1-methyl-1-propenyl)-6,6-dimethyl-1,4,7-trioxaspiro(4.4)nonane Structure

89983-29-9

(+/-)-(E)-8-(3-...

~%

7-[(E)-3-(5,5-dimethyl-4-oxooxolan-2-yl)but-2-enoxy]chromen-2-one Structure

98066-12-7

7-[(E)-3-(5,5-d...

N/A Structure

93741-03-8

N/A

~%

7-[(E)-3-(5,5-dimethyl-4-oxooxolan-2-yl)but-2-enoxy]chromen-2-one Structure

98066-12-7

7-[(E)-3-(5,5-d...

(E)-6,7-dihydroxy-3,7-dimethyl-2-octenyl benzyl ether Structure

68690-80-2

(E)-6,7-dihydro...

~97%

4-methyl-6-phenylmethoxyhex-4-enal Structure

32989-52-9

4-methyl-6-phen...


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