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A practical synthetic route to struc...

Brubaker, Jason Daniel.

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A practical synthetic route to structurally diverse tetracycline antibiotics.

紀錄類型:	書目-語言資料,印刷品 : Monograph/item
正題名/作者:	A practical synthetic route to structurally diverse tetracycline antibiotics./
作者:	Brubaker, Jason Daniel.
面頁冊數:	227 p.
附註:	Adviser: Andrew G. Myers.
Contained By:	Dissertation Abstracts International69-01B.
標題:	Chemistry, Organic. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3295903
ISBN:	9780549408260

A practical synthetic route to structurally diverse tetracycline antibiotics.
Brubaker, Jason Daniel.

A practical synthetic route to structurally diverse tetracycline antibiotics. - 227 p.

Adviser: Andrew G. Myers.

Thesis (Ph.D.)--Harvard University, 2008.

*Please refer to dissertation for diagrams.

ISBN: 9780549408260Subjects--Topical Terms:

516206
Chemistry, Organic.

A practical synthetic route to structurally diverse tetracycline antibiotics.
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245 1 2 $a A practical synthetic route to structurally diverse tetracycline antibiotics.
300 $a 227 p.
500 $a Adviser: Andrew G. Myers.
500 $a Source: Dissertation Abstracts International, Volume: 69-01, Section: B, page: 0319.
502 $a Thesis (Ph.D.)--Harvard University, 2008.
520 $a *Please refer to dissertation for diagrams.
520 $a A practical synthetic route to structurally diverse tetracycline antibiotics has been developed. Previously, enone 76 had been demonstrated to be a key precursor to (--)-6-deoxytetracycline (74) in a three-step sequence involving a Michael-Dieckmann reaction and deprotection. We have now demonstrated that enone 76 can be transformed into a diverse array of new tetracycline antibiotics, several of which (such as 151 and 152) show excellent activity in tetracycline-resistant Gram-positive and Gram-negative organisms.
520 $a Further exploration of structure activity relationships in the 6-deoxytetracycline series and, ultimately, clinical development of a drug candidate will require the production of kilogram quantities of enone 76. The previously developed route to 76 proceeded in 11 steps and 10% overall yield. We have now developed a completely different route to 76, which proceeds in 9 steps and 27% overall yield. Key features of the synthesis are the enantioselective addition of divinylzinc to aldehyde 188, the convergent coupling of allylic amine 183 with 3-methoxyfurfural (184), the endo-selective furan Diels--Alder reaction of 182, and the boron tribromide promoted demethylation and ring-opening of the oxabicyclic ring system within 208. Ultimately, the new route was used to produce 40 g of enone 76 in three weeks. While further process development will be necessary, this new route provides an excellent starting point for the kilogram-scale production of enone 76.*
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