Enantioselective Total Syntheses of Leuconolam–Leuconoxine–Mersicarpine Group Monoterpene Indole Alkaloids

A unified strategy allowing enantioselective total syntheses of (−)-mersicarpine, (−)-scholarisine G, (+)-melodinine E, (−)-leuconoxine, and (−)-leuconolam from a common cyclohexenone derivative was reported. The Suzuki–Miyaura reaction was used to couple two simple fragments incorporating the key e...

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Published inJournal of the American Chemical Society Vol. 135; no. 51; pp. 19127 - 19130
Main Authors Xu, Zhengren, Wang, Qian, Zhu, Jieping
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.12.2013
Amer Chemical Soc
Subjects
Alkaloids - chemical synthesis
Azepines - chemistry
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Multidisciplinary
Indole Alkaloids - chemistry
Models, Molecular
Molecular Structure
Monoterpenes - chemical synthesis
Monoterpenes - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
CONCISE
(-)-MERSICARPINE
FORMAL SYNTHESIS
(-)-RHAZINILAM
PRODUCTS
APOCYNACEAE
RING
(+/-)-MERSICARPINE
GRIFFITHII
ASPIDOSPERMA ALKALOIDS
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Summary:A unified strategy allowing enantioselective total syntheses of (−)-mersicarpine, (−)-scholarisine G, (+)-melodinine E, (−)-leuconoxine, and (−)-leuconolam from a common cyclohexenone derivative was reported. The Suzuki–Miyaura reaction was used to couple two simple fragments incorporating the key elements for total synthesis, and unprecedented oxidation/reduction/cyclization processes were developed that converted the substituted cyclohexenone to either a mersicarpine or leuconoxine skeleton. In a reverse biomimetic synthesis fashion, (+)-melodinine E was converted to (−)-leuconolam under acidic conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja4115192