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I. The asymmetric synthesis of the a...

Miller, Scott Joseph.

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I. The asymmetric synthesis of the antitumor antibiotic macbecin I. II. Chiral copper(II) complexes as Lewis acids in the asymmetric catalysis of the Diels-Alder reaction.

Record Type:	Electronic resources : Monograph/item
Title/Author:	I. The asymmetric synthesis of the antitumor antibiotic macbecin I. II. Chiral copper(II) complexes as Lewis acids in the asymmetric catalysis of the Diels-Alder reaction./
Author:	Miller, Scott Joseph.
Description:	212 p.
Notes:	Source: Dissertation Abstracts International, Volume: 55-08, Section: B, page: 3313.
Contained By:	Dissertation Abstracts International55-08B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9500101

I. The asymmetric synthesis of the antitumor antibiotic macbecin I. II. Chiral copper(II) complexes as Lewis acids in the asymmetric catalysis of the Diels-Alder reaction.
Miller, Scott Joseph.

I. The asymmetric synthesis of the antitumor antibiotic macbecin I. II. Chiral copper(II) complexes as Lewis acids in the asymmetric catalysis of the Diels-Alder reaction. - 212 p.

Source: Dissertation Abstracts International, Volume: 55-08, Section: B, page: 3313.

Thesis (Ph.D.)--Harvard University, 1994.

I: The asymmetric synthesis of the antitumor antibiotic macbecin I. A convergent asymmetric synthesis of the antitumor antibiotic macbecin I has been achieved through the synthesis and coupling of the aromatic synthon 16, the C5-C12 synthon 15 and the allyl phosphonate 23c. Six of the seven stereogenic centers within the target structure were controlled using asymmetric aldol methodology, while the final stereogenic center was set using internal stereocontrol. Union of 16 and 15 was accomplished using a very mild and high yielding titanium tetrachloride mediated aldol reaction. The C1-C5 unsaturated moiety was incorporated stereoselectively employing the phosphonate 23c in a kinetically controlled Horner-Emmons reaction. Macrolactamization and subsequent refunctionalization afforded (+)Subjects--Topical Terms:

516206
Chemistry, Organic.

I. The asymmetric synthesis of the antitumor antibiotic macbecin I. II. Chiral copper(II) complexes as Lewis acids in the asymmetric catalysis of the Diels-Alder reaction.
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035 $a (UnM)AAI9500101
035 $a AAI9500101
040 $a UnM $c UnM
100 1 $a Miller, Scott Joseph. $3 1928495
245 1 0 $a I. The asymmetric synthesis of the antitumor antibiotic macbecin I. II. Chiral copper(II) complexes as Lewis acids in the asymmetric catalysis of the Diels-Alder reaction.
300 $a 212 p.
500 $a Source: Dissertation Abstracts International, Volume: 55-08, Section: B, page: 3313.
502 $a Thesis (Ph.D.)--Harvard University, 1994.
520 $a I: The asymmetric synthesis of the antitumor antibiotic macbecin I. A convergent asymmetric synthesis of the antitumor antibiotic macbecin I has been achieved through the synthesis and coupling of the aromatic synthon 16, the C5-C12 synthon 15 and the allyl phosphonate 23c. Six of the seven stereogenic centers within the target structure were controlled using asymmetric aldol methodology, while the final stereogenic center was set using internal stereocontrol. Union of 16 and 15 was accomplished using a very mild and high yielding titanium tetrachloride mediated aldol reaction. The C1-C5 unsaturated moiety was incorporated stereoselectively employing the phosphonate 23c in a kinetically controlled Horner-Emmons reaction. Macrolactamization and subsequent refunctionalization afforded (+) $- $ macbecin I.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI)II: Chiral copper (II) complexes as Lewis acids in the asymmetric catalysis of the Diels-Alder reaction. Bis(oxazoline) and bis(imine) complexes of copper II (catalysts A and B) have been identified as Lewis acids in the asymmetric catalysis of the Diels-Alder reaction. The reaction has been demonstrated to proceed with a range of dienophiles (8 and 10, R=H, CH $\ sb3 $, Ph, COOEt) to afford cycloadducts 9 and 11 with high diastereoselectivities (endo/exo ratios up to 98:2) and enantioselectivities (up to $> $9 8% ee). The scope of the reaction has been expanded to include both cyclic and acyclic dienes. In addition, mechanistic studies were executed which suggest that the reaction proceeds through a square planar catalyst-substrate complex, wherein the imide substrates 8 and 10 bind to the metal center in a bidentate fashion.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI)
590 $a School code: 0084.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Inorganic. $3 517253
690 $a 0490
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710 2 0 $a Harvard University. $3 528741
773 0 $t Dissertation Abstracts International $g 55-08B.
790 $a 0084
791 $a Ph.D.
792 $a 1994
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9500101