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举例 :可输入Filippa Pettersson 或者 Cancer Res. 75(6) , 1102-12, (2015) 或者10.1002/anie.201600521

Stereocontrolled total synthesis of (.+-.)-pentenomycins. I-III, their epimers, and dehydropentenomycin I

…, SJ Branca, NN Pilla, MA Guaciaro

文献索引：Smith III; Branca; Pilla; Guaciaro Journal of Organic Chemistry, 1982 , vol. 47, # 10 p. 1855 - 1869

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被引用次数: 108

摘要

The total synthesis of (f)-pentenomycins 1-111 (la-c), their epimers (2a-c) termed by us epipentenomycins (I-111), and dehydropentenomycin I (3), seven members of the novel cyclopentanoid class of antibiotics, has been achieved. The synthetic routes are short (ca. five to seven steps), stereocontrolled, and for the most part highly efficient. Key elements of the strategies were (i) the development of a versatile a-ketovinyl anion equivalent which ...

2-溴环戊-2-烯酮结构式

2-溴环戊-2-烯酮

乙二醇结构式

~82%

1,4-DIOXASPIRO[4.4]NON-6-ENE, 6-BROMO-结构式

1,4-DIOXASPIRO[...

2-(羟甲基)环戊-2-烯酮结构式

2-(羟甲基)环戊-2-烯酮

乙酸酐结构式

~90%

Cyclopent-2-en-1-one, 2-acetyloxymethyl结构式

Cyclopent-2-en-...

6-carbethoxy-1,4-dioxaspiro[4.4]non-6-ene结构式

6-carbethoxy-1,...

~%

Cyclopent-2-en-1-one, 2-acetyloxymethyl结构式

Cyclopent-2-en-...

1,4-DIOXASPIRO[4.4]NON-6-ENE, 6-BROMO-结构式

1,4-DIOXASPIRO[...

~%

Cyclopent-2-en-1-one, 2-acetyloxymethyl结构式

Cyclopent-2-en-...

2-溴环戊-2-烯酮结构式

2-溴环戊-2-烯酮

~%

Cyclopent-2-en-1-one, 2-acetyloxymethyl结构式

Cyclopent-2-en-...

ethyl 5-oxocyclopentene-1-carboxylate结构式

ethyl 5-oxocycl...

~%

Cyclopent-2-en-1-one, 2-acetyloxymethyl结构式

Cyclopent-2-en-...

6-carbethoxy-1,4-dioxaspiro[4.4]non-6-ene结构式

6-carbethoxy-1,...

~%

2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopent-2-en-1-one结构式

2-[[tert-butyl(...

1,4-DIOXASPIRO[4.4]NON-6-ENE, 6-BROMO-结构式

1,4-DIOXASPIRO[...

~%

2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopent-2-en-1-one结构式

2-[[tert-butyl(...

2-溴环戊-2-烯酮结构式

2-溴环戊-2-烯酮

~%

2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopent-2-en-1-one结构式

2-[[tert-butyl(...

ethyl 5-oxocyclopentene-1-carboxylate结构式

ethyl 5-oxocycl...

~%

2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopent-2-en-1-one结构式

2-[[tert-butyl(...

cis-4,5-dihydroxy-5-[[(tert-butyldimethylsilyl)oxy]methyl]-2-cyclopentenone结构式

cis-4,5-dihydro...

~93%

2-Cyclopenten-1-one,4,5-dihydroxy-5-(hydroxymethyl)-, (4R,5R)-rel-结构式

2-Cyclopenten-1...

t-4-[(tert-butyldimethylsilyl)oxy]-5-hydroxy-r-5-[[(tert-butyldimethylsilyl)oxy]methyl]-2-cyclopentenone结构式

t-4-[(tert-buty...

~96%

2-Cyclopenten-1-one,4,5-dihydroxy-5-(hydroxymethyl)-, (4R,5R)-rel-结构式

2-Cyclopenten-1...

6-carbethoxy-1,4-dioxaspiro[4.4]non-6-ene结构式

6-carbethoxy-1,...

~%

2-Cyclopenten-1-one,4,5-dihydroxy-5-(hydroxymethyl)-, (4R,5R)-rel-结构式

2-Cyclopenten-1...

1,4-DIOXASPIRO[4.4]NON-6-ENE, 6-BROMO-结构式

1,4-DIOXASPIRO[...

~%

2-Cyclopenten-1-one,4,5-dihydroxy-5-(hydroxymethyl)-, (4R,5R)-rel-结构式

2-Cyclopenten-1...

2-溴环戊-2-烯酮结构式

2-溴环戊-2-烯酮

~%

2-Cyclopenten-1-one,4,5-dihydroxy-5-(hydroxymethyl)-, (4R,5R)-rel-结构式

2-Cyclopenten-1...

2-(羟甲基)环戊-2-烯酮结构式

2-(羟甲基)环戊-2-烯酮

~%

2-Cyclopenten-1-one,4,5-dihydroxy-5-(hydroxymethyl)-, (4R,5R)-rel-结构式

2-Cyclopenten-1...

2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopent-2-en-1-one结构式

2-[[tert-butyl(...

~%

2-Cyclopenten-1-one,4,5-dihydroxy-5-(hydroxymethyl)-, (4R,5R)-rel-结构式

2-Cyclopenten-1...

ethyl 5-oxocyclopentene-1-carboxylate结构式

ethyl 5-oxocycl...

~%

2-Cyclopenten-1-one,4,5-dihydroxy-5-(hydroxymethyl)-, (4R,5R)-rel-结构式

2-Cyclopenten-1...

cis-2,3-dihydroxy-2-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentanone结构式

cis-2,3-dihydro...

~%

2-Cyclopenten-1-one,4,5-dihydroxy-5-(hydroxymethyl)-, (4R,5R)-rel-结构式

2-Cyclopenten-1...

t-3-[(tert-butyldimethylsilyl)oxy]-2-hydroxy-r-2-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentanone结构式

t-3-[(tert-buty...

~%

2-Cyclopenten-1-one,4,5-dihydroxy-5-(hydroxymethyl)-, (4R,5R)-rel-结构式

2-Cyclopenten-1...

6-carbethoxy-1,4-dioxaspiro[4.4]non-6-ene结构式

6-carbethoxy-1,...

~%

2-(羟甲基)环戊-2-烯酮结构式

2-(羟甲基)环戊-2-烯酮

1,4-DIOXASPIRO[4.4]NON-6-ENE, 6-BROMO-结构式

1,4-DIOXASPIRO[...

~%

2-(羟甲基)环戊-2-烯酮结构式

2-(羟甲基)环戊-2-烯酮

2-溴环戊-2-烯酮结构式

2-溴环戊-2-烯酮

~%

2-(羟甲基)环戊-2-烯酮结构式

2-(羟甲基)环戊-2-烯酮

ethyl 5-oxocyclopentene-1-carboxylate结构式

ethyl 5-oxocycl...

~%

2-(羟甲基)环戊-2-烯酮结构式

2-(羟甲基)环戊-2-烯酮

2-溴-3-甲基-2-环戊烯-1-酮结构式

2-溴-3-甲基-2-环戊烯-1-酮

乙二醇结构式

~90%

9-bromo-8-methyl-1,4-dioxaspiro[4.4]non-8-ene结构式

9-bromo-8-methy...

3-甲基-2-环戊烯-1-酮结构式

3-甲基-2-环戊烯-1-酮

~%

9-bromo-8-methyl-1,4-dioxaspiro[4.4]non-8-ene结构式

9-bromo-8-methy...

环己烯酮结构式

~%

6-bromo-1,4-dioxaspiro[4.5]dec-6-ene结构式

6-bromo-1,4-dio...

2-溴环戊-2-烯酮结构式

2-溴环戊-2-烯酮

~%

2-methylsulfanylcyclopent-2-en-1-one结构式

2-methylsulfany...

1,4-DIOXASPIRO[4.4]NON-6-ENE, 6-BROMO-结构式

1,4-DIOXASPIRO[...

二甲基二硫醚结构式

二甲基二硫醚

~%

2-methylsulfanylcyclopent-2-en-1-one结构式

2-methylsulfany...

t-4-acetoxy-5-hydroxy-r-5-[[(tert-butyldimethylsilyl)oxy]methyl]-2-cyclopentenone结构式

t-4-acetoxy-5-h...

~88%

[5-hydroxy-5-(hydroxymethyl)-4-oxo-1-cyclopent-2-enyl] acetate结构式

[5-hydroxy-5-(h...

6-carbethoxy-1,4-dioxaspiro[4.4]non-6-ene结构式

6-carbethoxy-1,...

~%

[5-hydroxy-5-(hydroxymethyl)-4-oxo-1-cyclopent-2-enyl] acetate结构式

[5-hydroxy-5-(h...

1,4-DIOXASPIRO[4.4]NON-6-ENE, 6-BROMO-结构式

1,4-DIOXASPIRO[...

~%

[5-hydroxy-5-(hydroxymethyl)-4-oxo-1-cyclopent-2-enyl] acetate结构式

[5-hydroxy-5-(h...

2-溴环戊-2-烯酮结构式

2-溴环戊-2-烯酮

~%

[5-hydroxy-5-(hydroxymethyl)-4-oxo-1-cyclopent-2-enyl] acetate结构式

[5-hydroxy-5-(h...

2-(羟甲基)环戊-2-烯酮结构式

2-(羟甲基)环戊-2-烯酮

~%

[5-hydroxy-5-(hydroxymethyl)-4-oxo-1-cyclopent-2-enyl] acetate结构式

[5-hydroxy-5-(h...

2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopent-2-en-1-one结构式

2-[[tert-butyl(...

~%

[5-hydroxy-5-(hydroxymethyl)-4-oxo-1-cyclopent-2-enyl] acetate结构式

[5-hydroxy-5-(h...

ethyl 5-oxocyclopentene-1-carboxylate结构式

ethyl 5-oxocycl...

~%

[5-hydroxy-5-(hydroxymethyl)-4-oxo-1-cyclopent-2-enyl] acetate结构式

[5-hydroxy-5-(h...

cis-2,3-dihydroxy-2-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentanone结构式

cis-2,3-dihydro...

~%

[5-hydroxy-5-(hydroxymethyl)-4-oxo-1-cyclopent-2-enyl] acetate结构式

[5-hydroxy-5-(h...

cis-4,5-dihydroxy-5-[[(tert-butyldimethylsilyl)oxy]methyl]-2-cyclopentenone结构式

cis-4,5-dihydro...

~%

[5-hydroxy-5-(hydroxymethyl)-4-oxo-1-cyclopent-2-enyl] acetate结构式

[5-hydroxy-5-(h...

t-3-acetoxy-2-hydroxy-r-2-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentanone结构式

t-3-acetoxy-2-h...

~%

[5-hydroxy-5-(hydroxymethyl)-4-oxo-1-cyclopent-2-enyl] acetate结构式

[5-hydroxy-5-(h...

2-hydroxy-2-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopent-4-ene-1,3-dione结构式

2-hydroxy-2-[[(...

~75%

2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione结构式

2-hydroxy-2-(hy...

6-carbethoxy-1,4-dioxaspiro[4.4]non-6-ene结构式

6-carbethoxy-1,...

~%

2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione结构式

2-hydroxy-2-(hy...

1,4-DIOXASPIRO[4.4]NON-6-ENE, 6-BROMO-结构式

1,4-DIOXASPIRO[...

~%

2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione结构式

2-hydroxy-2-(hy...

2-溴环戊-2-烯酮结构式

2-溴环戊-2-烯酮

~%

2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione结构式

2-hydroxy-2-(hy...

2-(羟甲基)环戊-2-烯酮结构式

2-(羟甲基)环戊-2-烯酮

~%

2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione结构式

2-hydroxy-2-(hy...

2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclopent-2-en-1-one结构式

2-[[tert-butyl(...

~%

2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione结构式

2-hydroxy-2-(hy...

ethyl 5-oxocyclopentene-1-carboxylate结构式

ethyl 5-oxocycl...

~%

2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione结构式

2-hydroxy-2-(hy...

cis-4,5-dihydroxy-5-[[(tert-butyldimethylsilyl)oxy]methyl]-2-cyclopentenone结构式

cis-4,5-dihydro...

~%

2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione结构式

2-hydroxy-2-(hy...

cis-2,3-dihydroxy-2-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentanone结构式

cis-2,3-dihydro...

~%

2-hydroxy-2-(hydroxymethyl)cyclopent-4-ene-1,3-dione结构式

2-hydroxy-2-(hy...

6-carbethoxy-1,4-dioxaspiro[4.4]non-6-ene结构式

6-carbethoxy-1,...

~%

ethyl 5-oxocyclopentene-1-carboxylate结构式

ethyl 5-oxocycl...

A Convenient Procedure for the Synthesis of Acetals from α??...

[Carlson, Rolf; Gautun, Hanna; Westerlund, Andreas Advanced Synthesis and Catalysis, 2002 , vol. 344, # 1 p. 57 - 60]

Zinc-Mediated Highly α-Regioselective 1, 4-Addition of Chalc...

[Hanessian, Stephen; Mainetti, Emily; Lecomte, Fabien Organic Letters, 2006 , vol. 8, # 18 p. 4047 - 4049]

Highly Selective Methods for α-Alkenylation and α-Arylation ...

[Negishi, Ei-ichi; Akiyoshi, Kazunari Chemistry Letters, 1987 , p. 1007 - 1010]