Journal ArticleDOI
Diastereocontrol of the Claisen rearrangement by substituents external to the pericyclic array: synthetic studies on betaenone B and stemphyloxin I
Daniel V. Pratt,Paul B. Hopkins +1 more
TLDR
In this paper, the authors demonstrate that the stereochemical outcome of this type of rearrangements may be controlled by the spatial requirements of substituents external to the pericyclic array.About:
This article is published in Tetrahedron Letters.The article was published on 1987-01-01. It has received 18 citations till now. The article focuses on the topics: Claisen rearrangement & Pericyclic reaction.read more
Citations
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Journal ArticleDOI
The stereocontrolled formation of cyclic vicinal cis-diols via a samarium diiodide pinacol coupling of dialdehydes
TL;DR: Aliphatic 1,5-and 1,6 dialdehydes with and without α-substituents, as well as derivatives of carbohydrate dial dehydes undergo a pinacol coupling reaction in the presence of SmI 2 to give cis -diols as the preponderant products as mentioned in this paper.
Reference EntryDOI
Organocopper Reagents: Substitution, Conjugate Addition, Carbo/Metallocupration, and Other Reactions
TL;DR: In this paper, two reviews were contributed to the Organic Reactions series covering substitution and conjugate addition reactions in organocopper chemistry, and many solutions to this problem now exist.
Journal ArticleDOI
Total Synthesis of (+)-Epoxydictymene. Application of Alkoxy-Directed Cyclization to Diterpenoid Construction
TL;DR: In this paper, an enantioselective synthesis of (+)-epoxydictymene (1) is reported, which efficiently constructs the strained oxabicyclo[3.0] octane subunit of 1.3.
Journal ArticleDOI
Stereoselective smi2-mediated conversion of carbohydrates into cyclopentanols
TL;DR: In this article, the synthesis of cyclopentanols was effected by a zinc-assisted Grob-fragmentation, followed by a stereocontrolled SmI2-mediated cyclisation.
Journal ArticleDOI
Armed/Disarmed Effects and Adamantyl Expansion of Some Caged Tricyclic Acetals en Route to Tetrodotoxin1,2
TL;DR: Replacing the iodide of this product with an hydroxyl (32a --> 32b) by a free radical process has succeeded albeit in disappointing yield, Nevertheless the resulting hydroxy lactone is a promising synthon of the advanced Kishi-Goto intermediate.
References
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Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents
Journal ArticleDOI
Lanthanides in organic synthesis. 2. Reduction of .alpha.-heterosubstituted ketones
Gary A. Molander,Gregory Hahn +1 more
Journal ArticleDOI
Stereo- and regiochemistry of the Claisen rearrangement: applications to natural products synthesis
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