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Total syntheses of bistramide A and ...

Lowe, Jason T.

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Total syntheses of bistramide A and (-)-kendomycin.

紀錄類型:	書目-語言資料,印刷品 : Monograph/item
正題名/作者:	Total syntheses of bistramide A and (-)-kendomycin./
作者:	Lowe, Jason T.
面頁冊數:	428 p.
附註:	Adviser: James S. Panek.
Contained By:	Dissertation Abstracts International69-08B.
標題:	Chemistry, General. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3323132
ISBN:	9780549748779

Total syntheses of bistramide A and (-)-kendomycin.
Lowe, Jason T.

Total syntheses of bistramide A and (-)-kendomycin. - 428 p.

Adviser: James S. Panek.

Thesis (Ph.D.)--Boston University, 2009.

The focus of this dissertation involves the development of structurally diverse, enantioenriched crotylsilane reagents to be used in the formation of complex natural products. The first crotylsilane reagent to be examined bears a (Z)-olefinic bond. This reagent allows access to complementary stereochemical patterns to an earlier generation of silane reagents that bear (E)-olefin geometry. In addition, the preparation of a crotylsilane reagent bearing C-centered chirality where the stereocenter is fully substituted will also be detailed. Both reagents participate in Lewis acid-promoted [4+2]-annulations with aldehydes to provide stereochemically well-defined dihydropyrans.

ISBN: 9780549748779Subjects--Topical Terms:

1021807
Chemistry, General.

Total syntheses of bistramide A and (-)-kendomycin.
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245 1 0 $a Total syntheses of bistramide A and (-)-kendomycin.
300 $a 428 p.
500 $a Adviser: James S. Panek.
500 $a Source: Dissertation Abstracts International, Volume: 69-08, Section: B, page: .
502 $a Thesis (Ph.D.)--Boston University, 2009.
520 $a The focus of this dissertation involves the development of structurally diverse, enantioenriched crotylsilane reagents to be used in the formation of complex natural products. The first crotylsilane reagent to be examined bears a (Z)-olefinic bond. This reagent allows access to complementary stereochemical patterns to an earlier generation of silane reagents that bear (E)-olefin geometry. In addition, the preparation of a crotylsilane reagent bearing C-centered chirality where the stereocenter is fully substituted will also be detailed. Both reagents participate in Lewis acid-promoted [4+2]-annulations with aldehydes to provide stereochemically well-defined dihydropyrans.
520 $a Bistramide A was initially isolated in 1988 from Lissoclinum bistratum. Our interest in this molecule stems from the antiproliferative effects displayed against several human tumor cell lines having IC50 values in the sub-nanomolar range. In that regard, an enantioselective total synthesis of the marine metabolite bistramide A was carried out. The synthetic strategy relied on the use of three different organosilane reagents to construct all principal fragments while installing eight of the eleven stereogenic centers of the natural product. The synthesis of the C1-C13 fragment utilized an enantioenriched crotylsilane reagent that bears a (Z)-olefin. Previously described (E)-crotylsilane reagents allow access to the central gamma-amino acid residue and a segment of the spiroketal. Union of the three fragments, using peptide coupling strategies to assemble the carbon framework, completed the total synthesis of bistramide A.
520 $a (-)-Kendomycin is a structurally complex polyketide possessing a densely functionalized pyran and a unique quinone-methide chromophore. The natural product has shown promise in the treatment of osteoporosis, certain types of cancer and as a potent antibacterial agent. Kendomycin's unique chemical structure and bioactivity over a broad range of therapeutic areas has motivated us to initiate a study directed towards its total synthesis. Application of a custom designed enantioenriched crotylsilane reagent in a [4+2]-annulation provided access to the functionalized tetrahydropyran ring system of kendomycin. An intramolecular Barbier-type ring closure of an acyclic precursor containing the fully functionalized C-aryl glycoside and incipient ansa-bridging system produced the macrocycle. This material was used to complete the synthesis of kendomycin.
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650 4 $a Chemistry, Organic. $3 516206
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773 0 $t Dissertation Abstracts International $g 69-08B.
790 $a 0017
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