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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:	Language materials, manuscript : 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.
Description:	1 online resource (874 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 85-03, Section: B.
Contained By:	Dissertations Abstracts International85-03B.
Subject:	Hydrogenation. -
Online resource:	click for full text (PQDT)
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. - 1 online resource (874 pages)

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

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

Includes bibliographical references

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.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2024

Mode of access: World Wide Web

ISBN: 9798380267809Subjects--Topical Terms:

902568
Hydrogenation.
Index Terms--Genre/Form:

554714
Electronic books.

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