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Towards the synthesis of (-)-tetracycline; development of an approach initiated by the microbial dihydroxylation of benzoic acid.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Towards the synthesis of (-)-tetracycline; development of an approach initiated by the microbial dihydroxylation of benzoic acid.
作者:	Siegel, Dionicio Rhodes.
面頁冊數:	267 p.
附註:	Adviser: Andrew G. Myers.
附註:	Source: Dissertation Abstracts International, Volume: 64-05, Section: B, page: 2198.
Contained By:	Dissertation Abstracts International64-05B.
標題:	Chemistry, Organic.
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3091687
ISBN:	0496393960

Towards the synthesis of (-)-tetracycline; development of an approach initiated by the microbial dihydroxylation of benzoic acid.
Siegel, Dionicio Rhodes.

Towards the synthesis of (-)-tetracycline; development of an approach initiated by the microbial dihydroxylation of benzoic acid. [electronic resource] - 267 p.

Adviser: Andrew G. Myers.

Thesis (Ph.D.)--Harvard University, 2003.

*Please refer to dissertation for diagrams.

ISBN: 0496393960Subjects--Topical Terms:

193634
Chemistry, Organic.

Towards the synthesis of (-)-tetracycline; development of an approach initiated by the microbial dihydroxylation of benzoic acid.
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520 # $a *Please refer to dissertation for diagrams.
520 # $a A modular approach towards the laboratory synthesis of (-)-tetracycline (3) is described. The approach was initiated by microbial dihydroxylation of benzoic acid with the organism Alcaligenes eutrophus strain B9. This reaction provides diol 61 in >95% ee on scales of >100 g. The microbial dihydroxylation product 61 has been transformed in three or fewer steps into several useful synthetic intermediates. The epoxide 80, prepared by a novel allylic epoxide rearrangement reaction of epoxide 66, has been transformed in a six-step sequence into cyclohexenone 125, the key intermediate in our modular approach towards (-)-tetracycline (3).
520 # $a Attempts to convert 125 into (-)-tetracycline ( 3) using isobenzofuran Diels-Alder reactions were not successful. Subsequently cyclohexenone 125 underwent an o-quinone dimethide Diels-Alder reaction to provide enone 134, a product containing all the skeletal carbon atoms of (-)-tetracycline (3). An alternative means of generating the tetracyclic framework of (-)-tetracycline (3) in a single operation was achieved using a Michael addition-Dieckmann cyclization sequence, providing hydroquinone 141.*
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