Studies Toward the Total Synthesis of Discodermolide PDF Download
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Author: Ge Yang
Publisher:
ISBN:
Category :
Languages : en
Pages : 354
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Book Description
Author: Ge Yang
Publisher:
ISBN:
Category :
Languages : en
Pages : 354
Get Book Here
Book Description
![Application of the [2,3] Wittig Rearrangement to Synthetic Studies Toward the Total Synthesis of (+)-discodermolide PDF](https://books.google.com/books/content/images/frontcover/N3SwuAAACAAJ?fife=w80-h100)
Author: Guohua Liang
Publisher:
ISBN: 9780549042266
Category : Chemistry, Organic
Languages : en
Pages : 154
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Book Description
Background information and stereochemical consequences of the [2,3] Wittig rearrangement are discussed. Examples of the application of the [2,3] Wittig rearrangement to the total synthesis of natural products are described, as are previous total syntheses of (+)-discodermolide also presented.
Author: David Louis Clark
Publisher:
ISBN:
Category :
Languages : en
Pages : 338
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Author: Stephen P. Wren
Publisher:
ISBN:
Category :
Languages : en
Pages :
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Author: Alexander Arefolov
Publisher:
ISBN:
Category :
Languages : en
Pages : 396
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Abstract: An enantioselective total synthesis of the marine natural product (+)-discodermolide has been accomplished utilizing a highly convergent and stereocontrolled strategy. The C1-C24 fragment was constructed via a palladium-mediated sp 2 -sp 3 cross-coupling reaction between the C1-C14 vinyl iodide and the C15-C24 alkyl iodide subunits. The C1-C14 subunit was obtained using an acetate aldol reaction to construct the C6-C7 bond and install the C7 stereocenter with high levels of 1,5- anti stereoinduction. The key C13-C14 trisubstituted (Z)-olefin was prepared applying a novel hydrozirconation-cross-coupling methodology. The C1-C6, C7-C14 and C15-C24 subunits were synthesized using chiral silane-based asymmetric C-C bond construction methodology to introduce eight out of thirteen molecule's stereogenic centers. This synthesis illustrates the application of chiral crotylsilane bond construction methodology for the enantioselective synthesis of natural products and offers complementary approach to the aldol-based methodology. A highly flexible and stereoselective protocol for the synthesis of functionalized (Z)- and (E)-trisubstituted alkenes has been developed. The key steps are hydrozirconation-iodination of (1-alkynyl)trimethylsilane followed by Negishi-type cross-coupling. The resultant (Z)-vinyl silane is iododesilylated and subjected to the second cross-coupling to give the trisubstituted olefin. Model studies aimed at the construction of C13-C14 trisubstituted olefin of (+)-discodermolide are described.
Author: Lisa Deanna Julian
Publisher:
ISBN:
Category :
Languages : en
Pages : 416
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Author: Zhonghua Pei
Publisher:
ISBN:
Category :
Languages : en
Pages : 410
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Author: Scott S. Harried
Publisher:
ISBN:
Category :
Languages : en
Pages : 378
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Author: Adam Christopher Loy Yip
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ISBN:
Category :
Languages : en
Pages :
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Author: Jennie Beth Nerenberg
Publisher:
ISBN:
Category :
Languages : en
Pages : 400
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