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Exploration of salvinorin a Chemical...

Hill, Sarah J.,

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Exploration of salvinorin a Chemical Space /

Record Type:	Electronic resources : Monograph/item
Title/Author:	Exploration of salvinorin a Chemical Space // Sarah J Hill.
Author:	Hill, Sarah J.,
Description:	1 electronic resource (375 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 85-01, Section: B.
Contained By:	Dissertations Abstracts International85-01B.
Subject:	Chemistry. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=30527431
ISBN:	9798379779207

Exploration of salvinorin a Chemical Space /
Hill, Sarah J.,

Exploration of salvinorin a Chemical Space /Sarah J Hill. - 1 electronic resource (375 pages)

Source: Dissertations Abstracts International, Volume: 85-01, Section: B.

The salvinorins serve as templates for next generation analgesics, antipruritics and dissociative hallucinogens via selective and potent agonism of the kappa-opioid receptor (KOR). In contrast to most opioids, the salvinorins lack basic amines and bind with high affinity and selectivity via complex polyoxygenated scaffolds that have frustrated deep-seated modification by synthesis. Here we describe a short asymmetric synthesis that relies on a sterically-confined organocatalyst to dissociate acidity from reactivity and effect Robinson annulation of an unactivated nucleophile / unstable electrophile pair. Combined with a cobalt-catalyzed polarized diene-alkyne cycloaddition, the route allows divergent access to a focused library of salvinorins. We appraise the synthesis by its generation of multiple analogs that exceed the potency, selectivity, stability and functional bias of salvinorin A itself.

English

ISBN: 9798379779207Subjects--Topical Terms:

516420
Chemistry.
Subjects--Index Terms:

Chemistry

Exploration of salvinorin a Chemical Space /
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245 1 0 $a Exploration of salvinorin a Chemical Space / $c Sarah J Hill.
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300 $a 1 electronic resource (375 pages)
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500 $a Source: Dissertations Abstracts International, Volume: 85-01, Section: B.
500 $a Advisors: Shenvi, Ryan A. Committee members: Engle, Keary M.; Boger, Dale L.; Chen, Jason S.; Aube, Jeffrey.
502 $b Ph.D. $c The Scripps Research Institute $d 2024.
520 $a The salvinorins serve as templates for next generation analgesics, antipruritics and dissociative hallucinogens via selective and potent agonism of the kappa-opioid receptor (KOR). In contrast to most opioids, the salvinorins lack basic amines and bind with high affinity and selectivity via complex polyoxygenated scaffolds that have frustrated deep-seated modification by synthesis. Here we describe a short asymmetric synthesis that relies on a sterically-confined organocatalyst to dissociate acidity from reactivity and effect Robinson annulation of an unactivated nucleophile / unstable electrophile pair. Combined with a cobalt-catalyzed polarized diene-alkyne cycloaddition, the route allows divergent access to a focused library of salvinorins. We appraise the synthesis by its generation of multiple analogs that exceed the potency, selectivity, stability and functional bias of salvinorin A itself.
546 $a English
590 $a School code: 1179
650 4 $a Chemistry. $3 516420
650 4 $a Pharmaceutical sciences. $3 3173021
653 $a Chemistry
653 $a Organic chemistry
653 $a Salvinorins
653 $a Antipruritics
653 $a Kappa-opioid receptor
653 $a Analgesics
690 $a 0485
690 $a 0572
710 2 $a The Scripps Research Institute. $b Chemistry. $e degree granting institution. $3 3770438
720 1 $a Shenvi, Ryan A. $e degree supervisor.
773 0 $t Dissertations Abstracts International $g 85-01B.
790 $a 1179
791 $a Ph.D.
792 $a 2024
856 4 0 $u https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=30527431