Concise Asymmetric Total Synthesis of 9-<i>epi</i>-Sessilifoliamide J

Tuo, Shi‐Chuan; Ye, Jian‐Liang; Wang, Ai‐E; Huang, Shih-Chien; Huang, Pei‐Qiang

doi:10.1021/ol202140y

Cited by 23 publications

(24 citation statements)

References 75 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Finally, Huang reported the total synthesis of 9‐epi sessilifoliamide J using a SmI 2 ‐mediated reductive coupling of ketone 158 with methyl methacrylate as the final step (Scheme ) . In an alternative protocol, cross‐coupling with β‐bromo‐methacrylate, followed by hydrogenation and lactonization under acidic conditions, gave improved stereocontrol in this transformation.…”

Section: From Aldehydes and Ketonesmentioning

confidence: 99%

Radical Reactions in Alkaloid Synthesis: A Perspective from Carbon Radical Precursors

Bonjoch

Diaba

2020

Eur J Org Chem

View full text Add to dashboard Cite

The usefulness of radical reactions in alkaloid synthesis is reviewed from the perspective of the functional groups embedded in the molecular structure of synthetic intermediates, that act as precursors of carbon‐centered radicals in the construction of new C–C bonds. The functional groups featured are alkenes, alkynes, halides (alkyl, vinyl, aryl), xanthates, sulfides, selenides, aldehydes, ketones, carboxylic acid derivatives (selenoesters, haloacetamides), β‐dicarbonyl compounds, and α‐heterosubstituted nitrogen‐compounds. The use of nitrogen‐centered radicals for C–N bond formation is also covered. Among the variety of radical processes applied, the most predominant are the hydride reductive method (Sn, Si), atom transfer radical reactions (Cu, Ru, B), and single‐electron transfer radical reactions promoted by Sm, Ni, Fe, Mn, Ti, and Ag. This review showcases the role radical reactions have played in the recent development of new strategies in alkaloid synthesis, as well as the implementation of new radical procedures in demanding substrates.

show abstract

Section: From Aldehydes and Ketonesmentioning

confidence: 99%

Radical Reactions in Alkaloid Synthesis: A Perspective from Carbon Radical Precursors

Bonjoch

Diaba

2020

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…Huang and co-workers took advantage of a diastereoselective VMR for the creation of the tricyclic structure of the stemona alkaloid, 9-epi-sessilifoliamide J (144). 64 The piperidine core was synthesized through the reaction of bicyclic N,O-acetal 141 with 2-methylsilyloxyfuran 142, giving optimum results with TMSOTf as a Lewis acid. VMR adduct 143 was introduced into the synthetic sequence as a diastereoisomeric mixture, allowing the authors to obtain, in four steps, the complex natural product 144 (Scheme 46).…”

Section: Scheme 44 Total Synthesis Of Indolizidine Alkaloids 137a-dmentioning

confidence: 99%

A Decade of Advance in the Asymmetric Vinylogous Mannich Reaction

2016

View full text Add to dashboard Cite

When the principle of vinylogy is applied to imines as electrophiles, the so-called vinylogous Mannich reaction (VMR), γ-aminocarbonyl (such as butenolides) and β-aminocarbonyl compounds are generated in a very efficient manner. The asymmetric version of this vinylogous Mannich reaction gives access to highly functionalized chiral synthons, which are suitable for further transformations. The versatility of this methodology is exemplified with the synthesis of several alkaloids and natural products. 1 Introduction 2 Asymmetric Vinylogous Mannich Reactions (VMR) with 2-Silyloxyfurans and 2-Silyloxypyrroles 3 Asymmetric VMR with Acyclic Silyl Dienolates and Silyl Dienol Ketene Acetals 4 Asymmetric VMR with γ-Butenolides and γ-Butyrolactams 5 Asymmetric VMR with α,α-Dicyanoolefins 6 Miscellaneous Donors in Asymmetric VMR 7 Application of the VMR to Natural Product Synthesis 8 Conclusions

show abstract

“…In the exploration of an enantioselective synthesis of (-)stemoamide [14], Hong's group employed the asymmetric hydrogenation of alkynone 23 using Noyori's catalyst (24), giving rise to the optically pure alcohol 25 (Scheme 2). Subsequent homologation of 25 provided 26, which could be further converted to the bicyclic 20a/b as a pair of an inseparable mixture (cis/trans 3:1), according to the similar sequence.…”

Section: Stemoamide-typementioning

confidence: 99%

“…Natural Product Communications Vol. 10 (6) 2015Liu & Wang Synthesis of (-)-9-epi-stemoamide by Wipf et al[21].\ Synthesis of (-)-9-epi-sessilifoliamide J by Huang and co-workers[24]. Huang's synthesis of (-)-sessilifoliamide J[25].…”

mentioning

confidence: 99%

Recent Advances in the Synthesis of Stemona Alkaloids

Liu

Wang

2015

Natural Product Communications

View full text Add to dashboard Cite

Stemona alkaloids, featuring polycyclic structures and interesting bioactivities, constitute a distinct class from the Stemonaceae family. In this review, recent advances in the synthesis of these unique alkaloids are briefly discussed, highlighting the application of novel synthetic strategies to access the core structures, as well as creative solutions to the installation of multiple stereogenic centers. The literature reviewed in this article covers the publications from 2010 to November 2014, a period that witnessed the prosperity of the synthesis of Stemona alkaloids.

show abstract

Concise Asymmetric Total Synthesis of 9-epi-Sessilifoliamide J

Cited by 23 publications

References 75 publications

Radical Reactions in Alkaloid Synthesis: A Perspective from Carbon Radical Precursors

Radical Reactions in Alkaloid Synthesis: A Perspective from Carbon Radical Precursors

A Decade of Advance in the Asymmetric Vinylogous Mannich Reaction

Recent Advances in the Synthesis of Stemona Alkaloids

Contact Info

Product

Resources

About