e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

Total synthesis of seco-lateriflorone

EJ Tisdale, BG Vong, H Li, SH Kim, C Chowdhury…

Index: Tisdale, Eric J.; Vong, Binh G.; Li, Hongmei; Kim, Sun Hee; Chowdhury, Chinmay; Theodorakis, Emmanuel A. Tetrahedron, 2003 , vol. 59, # 35 p. 6873 - 6887

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Citation Number: 62

Abstract

A convergent strategy toward the synthesis of lateriflorone (5) is described. Our approach is based on biosynthetic considerations and draws on a sequence of prenylation, oxygenation and Claisen reactions for the construction of chromenequinone 6, and a tandem Claisen/Diels–Alder reaction cascade for the synthesis of caged tricycle 7. Union of fragments 6 and 7 led to the synthesis of seco-lateriflorone (49).

5,8-dimethoxy-2,2-dimethyl-2H-chromen-7-ol Structure

5,8-dimethoxy-2...

~10%

5,8-dimethoxy-2,2-dimethyl-3,4-dihydrochromen-7-ol Structure

5,8-dimethoxy-2...

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1,2,3-tris(phenylmethoxy)benzene Structure

1,2,3-tris(phen...

~45%

2,6-bis(phenylmethoxy)cyclohexa-2,5-diene-1,4-dione Structure

2,6-bis(phenylm...

Benzene,5-nitro-1,2,3-tris(phenylmethoxy) Structure

Benzene,5-nitro...

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Pyrogallol Structure

~%

2,6-bis(phenylmethoxy)cyclohexa-2,5-diene-1,4-dione Structure

2,6-bis(phenylm...

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Benzyl bromide Structure

~%

2,6-bis(phenylmethoxy)cyclohexa-2,5-diene-1,4-dione Structure

2,6-bis(phenylm...

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5-BROMO-2,4-DIHYDROXYBENZOIC ACID Structure

5-BROMO-2,4-DIH...

Acetone Structure

~62%

6-BROMO-7-HYDROXY-2,2-DIMETHYL-BENZO[1,3]DIOXIN-4-ONE Structure

6-BROMO-7-HYDRO...

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2,4-Dihydroxybenzoic acid Structure

2,4-Dihydroxybe...

~%

6-BROMO-7-HYDROXY-2,2-DIMETHYL-BENZO[1,3]DIOXIN-4-ONE Structure

6-BROMO-7-HYDRO...

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2,6-bis(phenylmethoxy)benzene-1,4-diol Structure

2,6-bis(phenylm...

methyl iodide Structure

~%

Benzene,2,5-dimethoxy-1,3-bis(phenylmethoxy) Structure

Benzene,2,5-dim...

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2,6-bis(phenylmethoxy)cyclohexa-2,5-diene-1,4-dione Structure

2,6-bis(phenylm...

~%

2,6-bis(phenylmethoxy)benzene-1,4-diol Structure

2,6-bis(phenylm...

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1,2,3-tris(phenylmethoxy)benzene Structure

1,2,3-tris(phen...

~%

2,6-bis(phenylmethoxy)benzene-1,4-diol Structure

2,6-bis(phenylm...

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Benzyl bromide Structure

~%

2,6-bis(phenylmethoxy)benzene-1,4-diol Structure

2,6-bis(phenylm...

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Pyrogallol Structure

~%

2,6-bis(phenylmethoxy)benzene-1,4-diol Structure

2,6-bis(phenylm...

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Benzyl bromide Structure

Pyrogallol Structure

~98%

1,2,3-tris(phenylmethoxy)benzene Structure

1,2,3-tris(phen...

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1,2,3-tris(phenylmethoxy)benzene Structure

1,2,3-tris(phen...

~49%

2,6-bis(phenylmethoxy)cyclohexa-2,5-diene-1,4-dione Structure

2,6-bis(phenylm...

Benzene,5-nitro-1,2,3-tris(phenylmethoxy) Structure

Benzene,5-nitro...

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Pyrogallol Structure

~%

Benzene,5-nitro-1,2,3-tris(phenylmethoxy) Structure

Benzene,5-nitro...

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Benzyl bromide Structure

~%

Benzene,5-nitro-1,2,3-tris(phenylmethoxy) Structure

Benzene,5-nitro...

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3-Chloro-3-methyl-1-butyne Structure

3-Chloro-3-meth...

6-BROMO-7-HYDROXY-2,2-DIMETHYL-BENZO[1,3]DIOXIN-4-ONE Structure

6-BROMO-7-HYDRO...

~89%

10-BROMO-2,2,6,6-TETRAMETHYL-2H-1,5,7-TRIOXA-PHENANTHREN-8-ONE Structure

10-BROMO-2,2,6,...

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2,4-Dihydroxybenzoic acid Structure

2,4-Dihydroxybe...

~%

10-BROMO-2,2,6,6-TETRAMETHYL-2H-1,5,7-TRIOXA-PHENANTHREN-8-ONE Structure

10-BROMO-2,2,6,...

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5-BROMO-2,4-DIHYDROXYBENZOIC ACID Structure

5-BROMO-2,4-DIH...

~%

10-BROMO-2,2,6,6-TETRAMETHYL-2H-1,5,7-TRIOXA-PHENANTHREN-8-ONE Structure

10-BROMO-2,2,6,...

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3-Methyl butynol Structure

3-Methyl butynol

~%

10-BROMO-2,2,6,6-TETRAMETHYL-2H-1,5,7-TRIOXA-PHENANTHREN-8-ONE Structure

10-BROMO-2,2,6,...

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