Tetrahedron

Total synthesis of the polyene macrolide dermostatin A

CJ Sinz, SD Rychnovsky

Index: Sinz, Christopher J; Rychnovsky, Scott D Tetrahedron, 2002 , vol. 58, # 32 p. 6561 - 6576

Full Text: HTML

Citation Number: 28

Abstract

Herein we provide full details of studies which culminated in the first total synthesis of the polyene macrolide dermostatin A, confirming our earlier stereochemical assignment. A highly convergent synthesis was developed, featuring the cyanohydrin acetonide method for polyol construction and a Stille approach to polyene introduction. The strategies and tactics developed en route should be of value for the preparation of other members of the ...

 Related Synthetic Route
Ethanol Structure

64-17-5

Ethanol

Butanoic acid, 3,4-dihydroxy-, methyl ester, (3R)- Structure

114819-45-3

Butanoic acid, ...

~68%

Ethyl (R)-4-bromo-3-hydroxybutanoate Structure

95310-94-4

Ethyl (R)-4-bro...

Structure

375827-15-9

~77%

Dermostatin A Structure

51053-36-2

Dermostatin A

(4R)-5-bromo-4-(tert-butyldimethylsilanyloxy)-2-(trimethylsilanyloxy)pent-1-ene Structure

375826-99-6

(4R)-5-bromo-4-...

~%

Dermostatin A Structure

51053-36-2

Dermostatin A

bis((4S,6R)-6-(bromomethyl)-2,2-dimethyl-1,3-dioxan-4-yl)methane Structure

375826-89-4

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

~%

Dermostatin A Structure

51053-36-2

Dermostatin A

(6R)-6-[(1R,2S)-4-benzyloxy-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile Structure

375826-90-7

(6R)-6-[(1R,2S)...

~%

Dermostatin A Structure

51053-36-2

Dermostatin A

(2R,4S,6S,8R)-1,9-dibromo-2,8-bis(tert-butyldimethylsilanyloxy)nonane-4,6-diol Structure

375827-02-4

(2R,4S,6S,8R)-1...

~%

Dermostatin A Structure

51053-36-2

Dermostatin A

Structure

375827-06-8

~%

Dermostatin A Structure

51053-36-2

Dermostatin A

Structure

375827-05-7

~%

Dermostatin A Structure

51053-36-2

Dermostatin A

Structure

375827-09-1

~%

Dermostatin A Structure

51053-36-2

Dermostatin A

Structure

475160-71-5

~%

Dermostatin A Structure

51053-36-2

Dermostatin A

(4R)-5-bromo-4-(tert-butyldimethylsilanyloxy)pentan-2-one Structure

475160-66-8

(4R)-5-bromo-4-...

~%

Dermostatin A Structure

51053-36-2

Dermostatin A

(2R,6R,8R)-1,9-dibromo-2,8-bis(tert-butyldimethylsilanyloxy)-6-hydroxynonan-4-one Structure

375827-01-3

(2R,6R,8R)-1,9-...

~%

Dermostatin A Structure

51053-36-2

Dermostatin A

(4R,6R)-6-((2R,3S)-5-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)pentan-2-yl)-4-(((4R,6S)-6-(((4S,6R)-6-(bromomethyl)-2,2-dimethyl-1,3-dioxan-4-yl)methyl)-2,2-dimethyl-1,3-dioxan-4-yl)methyl)-2,2-dimethyl-1,3-dioxane-4-carbonitrile Structure

375827-03-5

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

~%

Dermostatin A Structure

51053-36-2

Dermostatin A

Structure

375827-04-6

~%

Dermostatin A Structure

51053-36-2

Dermostatin A


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