Enantioselective Total Syntheses of Pentacyclic Homoproaporphine Alkaloids

Herein we report the first enantioselective total syntheses of pentacyclic homoproaporphine alkaloids by means of a route, which includes a tandem retro-oxa-Michael addition and nucleophilic substitution to generate the oxa-benzobicyclco[3.3.1]­nonane core structure, a Pictet–Spengler cyclization to...

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Published inOrganic letters Vol. 22; no. 19; pp. 7526 - 7530
Main Authors Pu, Liu-Yang, Yang, Fan, Chen, Ji-Qiang, Xiong, Ying, Bin, Huai-Yu, Xie, Jian-Hua, Zhou, Qi-Lin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.10.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
cyclization reactions
enantioselectivity
Lewis bases
moieties
oxidation
Physical Sciences
Science & Technology
FACILE ISOMERIZATION
ACCESS
CATALYTIC ASYMMETRIC HYDROGENATION
Online AccessGet full text
ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.0c02720

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Abstract Herein we report the first enantioselective total syntheses of pentacyclic homoproaporphine alkaloids by means of a route, which includes a tandem retro-oxa-Michael addition and nucleophilic substitution to generate the oxa-benzobicyclco[3.3.1]­nonane core structure, a Pictet–Spengler cyclization to construct the fused B and C rings, and sequential Baeyer–Villiger oxidation and pinacol-type cyclization to install the hydroxyl-lactol moiety of D ring. With this unified route, six pentacyclic homoproaporphine alkaloids have been synthesized enantioselectively.
AbstractList Herein we report the first enantioselective total syntheses of pentacyclic homoproaporphine alkaloids by means of a route, which includes a tandem retro-oxa-Michael addition and nucleophilic substitution to generate the oxa-benzobicyclco[3.3.1]­nonane core structure, a Pictet–Spengler cyclization to construct the fused B and C rings, and sequential Baeyer–Villiger oxidation and pinacol-type cyclization to install the hydroxyl-lactol moiety of D ring. With this unified route, six pentacyclic homoproaporphine alkaloids have been synthesized enantioselectively.
Herein we report the first enantioselective total syntheses of pentacyclic homoproaporphine alkaloids by means of a route, which includes a tandem retro-oxa-Michael addition and nucleophilic substitution to generate the oxa-benzobicyclco[3.3.1]nonane core structure, a Pictet–Spengler cyclization to construct the fused B and C rings, and sequential Baeyer–Villiger oxidation and pinacol-type cyclization to install the hydroxyl-lactol moiety of D ring. With this unified route, six pentacyclic homoproaporphine alkaloids have been synthesized enantioselectively.
Herein we report the first enantioselective total syntheses of pentacyclic homoproaporphine alkaloids by means of a route, which includes a tandem retro-oxa-Michael addition and nucleophilic substitution to generate the oxa-benzobicyclco[3.3.1]nonane core structure, a Pictet-Spengler cyclization to construct the fused B and C rings, and sequential Baeyer-Villiger oxidation and pinacol-type cyclization to install the hydroxyl-lactol moiety of D ring. With this unified route, six pentacyclic homoproaporphine alkaloids have been synthesized enantioselectively.Herein we report the first enantioselective total syntheses of pentacyclic homoproaporphine alkaloids by means of a route, which includes a tandem retro-oxa-Michael addition and nucleophilic substitution to generate the oxa-benzobicyclco[3.3.1]nonane core structure, a Pictet-Spengler cyclization to construct the fused B and C rings, and sequential Baeyer-Villiger oxidation and pinacol-type cyclization to install the hydroxyl-lactol moiety of D ring. With this unified route, six pentacyclic homoproaporphine alkaloids have been synthesized enantioselectively.
Author Chen, Ji-Qiang
Pu, Liu-Yang
Yang, Fan
Xie, Jian-Hua
Zhou, Qi-Lin
Bin, Huai-Yu
Xiong, Ying
AuthorAffiliation State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry
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Snippet Herein we report the first enantioselective total syntheses of pentacyclic homoproaporphine alkaloids by means of a route, which includes a tandem...
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SubjectTerms Chemistry
Chemistry, Organic
cyclization reactions
enantioselectivity
Lewis bases
moieties
oxidation
Physical Sciences
Science & Technology
Title Enantioselective Total Syntheses of Pentacyclic Homoproaporphine Alkaloids
URI http://dx.doi.org/10.1021/acs.orglett.0c02720
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https://www.ncbi.nlm.nih.gov/pubmed/32937077
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