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Total syntheses of prenylflavonoids ...

Qi, Chao.

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Total syntheses of prenylflavonoids and polyketide-derived natural products.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Total syntheses of prenylflavonoids and polyketide-derived natural products./
作者:	Qi, Chao.
出版者:	Ann Arbor : ProQuest Dissertations & Theses, : 2017,
面頁冊數:	415 p.
附註:	Source: Dissertations Abstracts International, Volume: 78-09, Section: B.
Contained By:	Dissertations Abstracts International78-09B.
標題:	Organic chemistry. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10193586
ISBN:	9781369654530

Total syntheses of prenylflavonoids and polyketide-derived natural products.
Qi, Chao.

Total syntheses of prenylflavonoids and polyketide-derived natural products. - Ann Arbor : ProQuest Dissertations & Theses, 2017 - 415 p.

Source: Dissertations Abstracts International, Volume: 78-09, Section: B.

Thesis (Ph.D.)--Boston University, 2017.

This item must not be sold to any third party vendors.

Concise syntheses of the natural products brosimones A and B have been achieved using sequential dehydrogenative Diels-Alder (DHDA) cycloadditions. The syntheses employ either Pt/C-cyclopentene or DDQ to effect dehydrogenation of prenylchalcone substrates in combination with silver nanoparticles (AgNP's) to promote subsequent Diels-Alder cycloadditions. A concise, biomimetic approach to sorbiterrin A has been developed employing consecutive Michael additions of a 4-hydroxypyrone to a sorbicillinol derivative and silver nanoparticle-mediated bridged aldol/dehydration to construct the [3.3.1] ring system. The relative stereochemistry of sorbiterrin A was unambiguously confirmed by X-ray crystallographic analysis. Metal-catalyzed, double Claisen rearrangement of a bis-allyloxyflavone has been utilized to enable a concise synthesis of the hydrobenzofuro[3,2-b]chromenone core structure of the natural products sanggenon A and sanggenol F. In addition, catalytic, enantioselective [4+2] cycloadditions of 2'-hydroxychalcones have been accomplished using B(OPh)3/BINOL complexes. Asymmetric syntheses of the flavonoid Diels-Alder natural products sanggenons C and O have been achieved employing a stereodivergent reaction of a racemic mixture (stereodivergent RRM) involving [4+2] cycloaddition. Diaporine is a natural product containing a novel epoxyquinol dimer framework. An efficient annulation involving pyrone addition to a quinone has been developed for rapid assembly of the γ-naphthopyrone core structure. Dimerization was achieved through a Pd(II)-mediated dehydrogenative coupling. A natural product and precursor to diaporine, aurofusarin, was synthesized in excellent yield through an oxidation and demethylation sequence. In addition, diastereoselective epoxidation of aurofusarin was achieved using a phase transfer catalytic system.

ISBN: 9781369654530Subjects--Topical Terms:

523952
Organic chemistry.

Total syntheses of prenylflavonoids and polyketide-derived natural products.
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520 $a Concise syntheses of the natural products brosimones A and B have been achieved using sequential dehydrogenative Diels-Alder (DHDA) cycloadditions. The syntheses employ either Pt/C-cyclopentene or DDQ to effect dehydrogenation of prenylchalcone substrates in combination with silver nanoparticles (AgNP's) to promote subsequent Diels-Alder cycloadditions. A concise, biomimetic approach to sorbiterrin A has been developed employing consecutive Michael additions of a 4-hydroxypyrone to a sorbicillinol derivative and silver nanoparticle-mediated bridged aldol/dehydration to construct the [3.3.1] ring system. The relative stereochemistry of sorbiterrin A was unambiguously confirmed by X-ray crystallographic analysis. Metal-catalyzed, double Claisen rearrangement of a bis-allyloxyflavone has been utilized to enable a concise synthesis of the hydrobenzofuro[3,2-b]chromenone core structure of the natural products sanggenon A and sanggenol F. In addition, catalytic, enantioselective [4+2] cycloadditions of 2'-hydroxychalcones have been accomplished using B(OPh)3/BINOL complexes. Asymmetric syntheses of the flavonoid Diels-Alder natural products sanggenons C and O have been achieved employing a stereodivergent reaction of a racemic mixture (stereodivergent RRM) involving [4+2] cycloaddition. Diaporine is a natural product containing a novel epoxyquinol dimer framework. An efficient annulation involving pyrone addition to a quinone has been developed for rapid assembly of the γ-naphthopyrone core structure. Dimerization was achieved through a Pd(II)-mediated dehydrogenative coupling. A natural product and precursor to diaporine, aurofusarin, was synthesized in excellent yield through an oxidation and demethylation sequence. In addition, diastereoselective epoxidation of aurofusarin was achieved using a phase transfer catalytic system.
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