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Enantioselective Syntheses of Tetrah...

Kim, Alexia Nahyun.

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Enantioselective Syntheses of Tetrahydroisoquinolines (Thiqs) Via Iridium-Catalyzed Asymmetric Hydrogenation and Progress Toward the Total Synthesis of (+)-Cyanocycline A.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Enantioselective Syntheses of Tetrahydroisoquinolines (Thiqs) Via Iridium-Catalyzed Asymmetric Hydrogenation and Progress Toward the Total Synthesis of (+)-Cyanocycline A./
Author:	Kim, Alexia Nahyun.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2023,
Description:	874 p.
Notes:	Source: Dissertations Abstracts International, Volume: 85-03, Section: B.
Contained By:	Dissertations Abstracts International85-03B.
Subject:	Hydrogenation. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=30604341
ISBN:	9798380267809

Enantioselective Syntheses of Tetrahydroisoquinolines (Thiqs) Via Iridium-Catalyzed Asymmetric Hydrogenation and Progress Toward the Total Synthesis of (+)-Cyanocycline A.
Kim, Alexia Nahyun.

Enantioselective Syntheses of Tetrahydroisoquinolines (Thiqs) Via Iridium-Catalyzed Asymmetric Hydrogenation and Progress Toward the Total Synthesis of (+)-Cyanocycline A. - Ann Arbor : ProQuest Dissertations & Theses, 2023 - 874 p.

Source: Dissertations Abstracts International, Volume: 85-03, Section: B.

Thesis (Ph.D.)--California Institute of Technology, 2023.

Described herein are two reviews and three projects related to the asymmetric syntheses of tetrahydroisoquinoline (THIQs) alkaloids, and the progress toward the total synthesis of (+)-cyanocycline A. In Chapter 1, a review of the development of asymmetric methodologies for the preparation of enantioenriched N-heteroarenes is detailed. In Chapter 2, the development of an iridium-catalyzed enantio- and diastereoselective hydrogenation of 1,3-disubstituted isoquinolines to achieve cis-THIQs is reported. Chapter 3 describes the iridium-catalyzed asymmetric hydrogenation of 1,3-disubstituted isoquinolines that can afford trans-THIQs in a single transformation. Preliminary mechanistic insights to the iridium-catalyzed asymmetric hydrogenation method using deuterium experiments are detailed.Chapter 4 details a comprehensive review of the advances in the total syntheses of complex THIQ alkaloids from 2000 - 2020, ranging from simple benzyl THIQ natural products to complex THIQ alkaloids such as Ecteinascidin-743. In Chapter 5, efforts toward the total synthesis of (+)-cyanocycline A are described, harnessing a nonbiomimetic synthetic route through a convergent cross-coupling of two heterocyclic fragments followed by a global hydrogenation event.

ISBN: 9798380267809Subjects--Topical Terms:

1244863
Hydrogenation.

Enantioselective Syntheses of Tetrahydroisoquinolines (Thiqs) Via Iridium-Catalyzed Asymmetric Hydrogenation and Progress Toward the Total Synthesis of (+)-Cyanocycline A.
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