Journal ArticleDOI
Enantioselective Total Synthesis of (+)-Neostenine
Yasuaki Nakayama,Yuichiro Maeda,Masayuki Kotatsu,Ruriko Sekiya,Masato Ichiki,Takaaki Sato,Noritaka Chida +6 more
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TLDR
The SmI2 -mediated cyclization and the subsequent chemoselective reduction of a lactam moiety accomplished the first enantioselectives total synthesis of (+)-neostenine (1).Abstract:
A chirality transfer approach using acyclic polyol intermediates for the synthesis of (+)-neostenine (1) has been developed. The sequential Overman/Claisen rearrangement of an allylic 1,2-diol was especially useful, installing two contiguous stereocenters with complete diastereoselectivity in a one-pot sequence. The SmI2 -mediated cyclization and the subsequent chemoselective reduction of a lactam moiety accomplished the first enantioselective total synthesis of (+)-neostenine (1).read more
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Chemoselective reduction of carboxamides
TL;DR: This tutorial review provides an overview of the recent progress made in the development of chemoselective protocols for amide reduction and gives an insight to their advantages and drawbacks.
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Total Syntheses of Daphenylline, Daphnipaxianine A, and Himalenine D
TL;DR: Inspired by the proposed biosynthetic relationship between 1 and another calyciphylline A type alkaloid, a ring-expansion/aromatization/aldol cascade and versatile triketone intermediate were developed to construct the tetrasubstituted benzene moiety of 1.
Journal ArticleDOI
Catalytic Reductive Functionalization of Tertiary Amides using Vaska’s Complex: Synthesis of Complex Tertiary Amine Building Blocks and Natural Products
Daniel Matheau-Raven,Pablo Gabriel,Jamie A. Leitch,Yaseen A. Almehmadi,Ken Yamazaki,Darren J. Dixon +5 more
TL;DR: The tertiary amide is a ubiquitous functional group and plays an irreplaceable role in medicinal chemistry as discussed by the authors, and its robust nature has meant that selective manipulation of this motif remaine...
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Total Syntheses of Bisdehydroneostemoninine and Bisdehydrostemoninine by Catalytic Carbonylative Spirolactonization
TL;DR: The first total syntheses of the stemona alkaloids bis dehydroneostemoninine and bisdehydrostemoninine in racemic forms have been achieved using a novel palladium-catalyzed carbonylative spirolactonization of a hydroxycyclopropanol to rapidly construct the oxaspirolactic moiety.
Journal ArticleDOI
Recent advances in the Overman rearrangement: synthesis of natural products and valuable compounds
TL;DR: The Overman rearrangement has tremendous potential for rapid modification of various amino compounds and can be combined with other Claisen-rearrangements or other reactions for one-pot processes for further exploration.
References
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Journal ArticleDOI
Cascade reactions in total synthesis.
TL;DR: The power of cascade reactions in total synthesis is illustrated in the construction of complex molecules and underscore their future potential in chemical synthesis.
Journal ArticleDOI
Kaskadenreaktionen in der Totalsynthese
Kyriacos C. Nicolaou,Kyriacos C. Nicolaou,David J. Edmonds,David J. Edmonds,Paul G. Bulger,Paul G. Bulger +5 more
TL;DR: In this article, ausgewahlte Kaskadenreaktionen in der Naturstoffsynthese erlautert, wobei neuere Anwendungen besonders hervorgehoben werden.
Journal ArticleDOI
Samarium(II)-iodide-mediated cyclizations in natural product synthesis.
TL;DR: A review, cyclization reactions in natural product synthesis of 4-9 membered and larger rings were discussed.