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Literature DB >> 15200317

Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (+/-)-epi-zephyranthine.

Abstract

[reaction: see text] A new strategy for epi-zephyranthine has been developed that is based in part on an extraordinarily facile intramolecular Diels-Alder reaction of a 2-imido-substituted furan. By using a Rh(I)-catalyzed ring opening of the resulting oxabicyclic adduct, the cis-diol stereochemistry of epi-zephyranthine was established.

Entities: Chemical

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Year: 2004 PMID： 15200317 DOI： 10.1021/ol049348f

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

8 in total

1. Total synthesis of (+/-)-strychnine via a [4 + 2]-cycloaddition/rearrangement cascade.

Authors: Hongjun Zhang; Jutatip Boonsombat; Albert Padwa
Journal: Org Lett Date: 2007-01-18 Impact factor: 6.005

2. Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

Authors: Carolyn A Leverett; Michael P Cassidy; Albert Padwa
Journal: J Org Chem Date: 2006-10-27 Impact factor: 4.354

3. Synthesis of hydronaphthalenes through coupling of enyne carbonyl compounds that contain pendant alkene groups with Fischer carbene complexes.

Authors: Rajesh Kumar-Patti; Shaofeng Duan; Alejandro Camacho-Davila; Kris Waynant; Kenneth A Dunn; James W Herndon
Journal: Tetrahedron Lett Date: 2010-05-20 Impact factor: 2.415

4. Rhodium(I)-catalyzed nucleophilic ring-opening reactions of oxabicyclo adducts derived from the [4 + 2]-cycloaddition of 2-imido-substituted furans.

Authors: Albert Padwa; Qiu Wang
Journal: J Org Chem Date: 2006-04-14 Impact factor: 4.354

Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (+/-)-epi-zephyranthine.

1. Total synthesis of (+/-)-strychnine via a [4 + 2]-cycloaddition/rearrangement cascade.

2. Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

3. Synthesis of hydronaphthalenes through coupling of enyne carbonyl compounds that contain pendant alkene groups with Fischer carbene complexes.

4. Rhodium(I)-catalyzed nucleophilic ring-opening reactions of oxabicyclo adducts derived from the [4 + 2]-cycloaddition of 2-imido-substituted furans.

Review 5. Chemical and biological aspects of Narcissus alkaloids.

6. An efficient synthesis of (+/-)-Lycoricidine featuring a Stille-IMDAF cycloaddition cascade.

7. Synthesis of some members of the hydroxylated phenanthridone subclass of the Amaryllidaceae alkaloid family.

8. Synthesis of the erythrina alkaloid 3-demethoxyerythratidinone. Novel acid-induced rearrangements of its precursors.