東華大學圖書館 |

Language: English

Help

回圖書館首頁

手機版館藏查詢

Back

Switch To: Labeled | MARC Mode | ISBD

Linked to FindBook

Google Book

Amazon

博客來

α-Heteroatom Nitriles as Trianion Synthons : = Synthesis of Spirocyclic Heterocycles and the Lepadiformine Alkaloids.

Record Type:	Electronic resources : Monograph/item
Title/Author:	α-Heteroatom Nitriles as Trianion Synthons :/
Reminder of title:	Synthesis of Spirocyclic Heterocycles and the Lepadiformine Alkaloids.
Author:	Perry, Matthew A.
Description:	1 online resource (241 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 75-02, Section: B.
Contained By:	Dissertations Abstracts International75-02B.
Subject:	Chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3565861click for full text (PQDT)
ISBN:	9781303161605

α-Heteroatom Nitriles as Trianion Synthons : = Synthesis of Spirocyclic Heterocycles and the Lepadiformine Alkaloids.
Perry, Matthew A.

α-Heteroatom Nitriles as Trianion Synthons :Synthesis of Spirocyclic Heterocycles and the Lepadiformine Alkaloids. - 1 online resource (241 pages)

Source: Dissertations Abstracts International, Volume: 75-02, Section: B.

Thesis (Ph.D.)--University of California, Irvine, 2013.

Includes bibliographical references

The first part of the dissertation describes the total synthesis of the lepadiformine alkaloids A, B, and C. The key bond forming reactions involve a one-pot nitrile anion double alkylation and reductive decyanation/cyclization. The double alkylation was exploited to stereoselectively form the cyclohexyl C ring using an achiral aminonitrile and chiral dibromide electrophile. The reductive cyclization was utilized in the diastereoselective construction of the spiropyrrolidine motif. The spirocyclization proceeded by a double SEinv sequence to provide the spiropyrrolidine with overall retention of stereochemistry at the nitrile bearing carbon. The second portion details the extension of the double alkylation/reductive cyclization approach to the synthesis of various spirocyclic heterocycles. Simple achiral spirocycles of various ring sizes were explored. The construction of chiral substrates was also investigated to determine the diastereoselectivity concerning the double alkylation as well as the reductive cyclization. The diastereoselectivity for the double alkylation was low to moderate. The reductive cyclization proceeded with high diastereoselectivity for six membered nitrile bearing ring systems. The final chapter tells of the initial findings concerning two separate projects both involving reductive lithiation. The first details the reductive decyanation of decalin and hydrindane substrates that contain a nitrile at the ring junction carbon. The second involves the reductive lithiation and cyclization of tertiary organolithiums onto a pendent fluoride electrophile.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2023

Mode of access: World Wide Web

ISBN: 9781303161605Subjects--Topical Terms:

516420
Chemistry.
Subjects--Index Terms:

AlkaloidsIndex Terms--Genre/Form:

542853
Electronic books.

α-Heteroatom Nitriles as Trianion Synthons : = Synthesis of Spirocyclic Heterocycles and the Lepadiformine Alkaloids.
LDR:03166nmm a2200433K 4500 001 2362611
005 20231102121843.5
006 m o d
007 cr mn ---uuuuu
008 241011s2013 xx obm 000 0 eng d
020 $a 9781303161605
035 $a (MiAaPQ)AAI3565861
035 $a (MiAaPQ)uci:12217
035 $a AAI3565861
040 $a MiAaPQ $b eng $c MiAaPQ $d NTU
100 1 $a Perry, Matthew A. $3 3703355
245 1 0 $a α-Heteroatom Nitriles as Trianion Synthons : $b Synthesis of Spirocyclic Heterocycles and the Lepadiformine Alkaloids.
264 0 $c 2013
300 $a 1 online resource (241 pages)
336 $a text $b txt $2 rdacontent
337 $a computer $b c $2 rdamedia
338 $a online resource $b cr $2 rdacarrier
500 $a Source: Dissertations Abstracts International, Volume: 75-02, Section: B.
500 $a Publisher info.: Dissertation/Thesis.
500 $a Advisor: Rychnovsky, Scott D.
502 $a Thesis (Ph.D.)--University of California, Irvine, 2013.
504 $a Includes bibliographical references
520 $a The first part of the dissertation describes the total synthesis of the lepadiformine alkaloids A, B, and C. The key bond forming reactions involve a one-pot nitrile anion double alkylation and reductive decyanation/cyclization. The double alkylation was exploited to stereoselectively form the cyclohexyl C ring using an achiral aminonitrile and chiral dibromide electrophile. The reductive cyclization was utilized in the diastereoselective construction of the spiropyrrolidine motif. The spirocyclization proceeded by a double SEinv sequence to provide the spiropyrrolidine with overall retention of stereochemistry at the nitrile bearing carbon. The second portion details the extension of the double alkylation/reductive cyclization approach to the synthesis of various spirocyclic heterocycles. Simple achiral spirocycles of various ring sizes were explored. The construction of chiral substrates was also investigated to determine the diastereoselectivity concerning the double alkylation as well as the reductive cyclization. The diastereoselectivity for the double alkylation was low to moderate. The reductive cyclization proceeded with high diastereoselectivity for six membered nitrile bearing ring systems. The final chapter tells of the initial findings concerning two separate projects both involving reductive lithiation. The first details the reductive decyanation of decalin and hydrindane substrates that contain a nitrile at the ring junction carbon. The second involves the reductive lithiation and cyclization of tertiary organolithiums onto a pendent fluoride electrophile.
533 $a Electronic reproduction. $b Ann Arbor, Mich. : $c ProQuest, $d 2023
538 $a Mode of access: World Wide Web
650 4 $a Chemistry. $3 516420
650 4 $a Organic chemistry. $3 523952
653 $a Alkaloids
653 $a Heteroatom nitriles
653 $a Lepadiformine
653 $a Nitrile anion alkylation
653 $a Organolithium
653 $a Reductive lithiation
653 $a Spirocyclic heterocycles
655 7 $a Electronic books. $2 lcsh $3 542853
690 $a 0485
690 $a 0490
710 2 $a ProQuest Information and Learning Co. $3 783688
710 2 $a University of California, Irvine. $b Chemistry - Ph.D.. $3 2094938
773 0 $t Dissertations Abstracts International $g 75-02B.
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3565861 $z click for full text (PQDT)