國立高雄大學圖資館 |

Language: English

Back

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

Record Type:	Electronic resources : Monograph/item
Title/Author:	Towards the synthesis of (-)-tetracycline; development of an approach initiated by the microbial dihydroxylation of benzoic acid.
Author:	Siegel, Dionicio Rhodes.
Description:	267 p.
Notes:	Adviser: Andrew G. Myers.
Notes:	Source: Dissertation Abstracts International, Volume: 64-05, Section: B, page: 2198.
Contained By:	Dissertation Abstracts International64-05B.
Subject:	Chemistry, Organic.
Online resource:	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.
LDR:02227nmm _2200277 _450 001 162037
005 20051017073404.5
008 230606s2003 eng d
020 $a 0496393960
035 $a 00148538
035 $a 162037
040 $a UnM $c UnM
100 0 $a Siegel, Dionicio Rhodes. $3 227141
245 1 0 $a Towards the synthesis of (-)-tetracycline; development of an approach initiated by the microbial dihydroxylation of benzoic acid. $h [electronic resource]
300 $a 267 p.
500 $a Adviser: Andrew G. Myers.
500 $a Source: Dissertation Abstracts International, Volume: 64-05, Section: B, page: 2198.
502 $a Thesis (Ph.D.)--Harvard University, 2003.
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.*
590 $a School code: 0084.
650 # 0 $a Chemistry, Organic. $3 193634
710 0 # $a Harvard University. $3 212445
773 0 # $g 64-05B. $t Dissertation Abstracts International
790 $a 0084
790 1 0 $a Myers, Andrew G., $e advisor
791 $a Ph.D.
792 $a 2003
856 4 0 $u http://libsw.nuk.edu.tw/login?url=http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3091687 $z http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3091687