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The total syntheses of Delta(1)-Tetrahydrocannabinol and coronafacic acid.

Record Type:	Electronic resources : Monograph/item
Title/Author:	The total syntheses of Delta(1)-Tetrahydrocannabinol and coronafacic acid.
Author:	Shaughnessy, Eileen Anne.
Description:	167 p.
Notes:	Adviser: David A. Evans.
Notes:	Source: Dissertation Abstracts International, Volume: 64-05, Section: B, page: 2198.
Contained By:	Dissertation Abstracts International64-05B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3091681
ISBN:	0496393901

The total syntheses of Delta(1)-Tetrahydrocannabinol and coronafacic acid.
Shaughnessy, Eileen Anne.

The total syntheses of Delta(1)-Tetrahydrocannabinol and coronafacic acid. [electronic resource] - 167 p.

Adviser: David A. Evans.

Thesis (Ph.D.)--Harvard University, 2003.

*Please refer to dissertation for diagrams.

ISBN: 0496393901Subjects--Topical Terms:

193634
Chemistry, Organic.

The total syntheses of Delta(1)-Tetrahydrocannabinol and coronafacic acid.
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245 1 4 $a The total syntheses of Delta(1)-Tetrahydrocannabinol and coronafacic acid. $h [electronic resource]
300 $a 167 p.
500 $a Adviser: David A. Evans.
500 $a Source: Dissertation Abstracts International, Volume: 64-05, Section: B, page: 2198.
502 $a Thesis (Ph.D.)--Harvard University, 2003.
520 # $a *Please refer to dissertation for diagrams.
520 # $a I. The total synthesis of Delta1-Tetrahydrocannabinol . The total synthesis of Delta1-Tetrahydrocannabinol (THC) has been achieved in 5 steps and 21% overall yield from a simple acrylimide. The key step of the synthesis is an enantioselective Diels-Alder reaction catalyzed by a Cu(II) bis(oxazoline) complex. This synthesis delivers THC free of contamination from isomeric cannabinoids, which has been reported to be a problem in previous syntheses. This is the first enantioselective synthesis of THC in which the stereocenters do not arise directly from the chiral pool.*
520 # $a II. The Diels-Alder reaction of alpha,beta-unsaturated beta-ketoimides . Unsaturated beta-ketoimides have been used as electrophiles in the aluminum-mediated Diels-Alder reaction of cyclopentadiene, cyclohexadiene, trans-piperylene, and isoprene. The cyclic products are formed with high diastereoselectivity. A representative cycloadduct was decarboxylated to provide a cyclic chiral ketone building block.*
520 # $a III. The total synthesis of (+)-coronafacic acid. The total synthesis of (+)-coronafacic acid has been accomplished in 16 steps and 14% overall yield from bisphenoxyphosphonoacetate. The Z ester diene functionality was constructed in high yield and selectivity using an allylic phosphonate reagent. Both the boron- and magnesium-mediated aldol additions provide aldol products with high diastereoselectivity. Oxidation of the aldol adducts, followed by oxidation and Diels-Alder reaction, provides the hydrindane ring system. Oxazolidinone cleavage and decarboxylation, followed by oxidation, provides the natural product.*
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