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Literature DB >> 16805534

Origins of selectivity in pericyclic reaction cascades for the synthesis of gambogin and lateriflorone.

Amy E Hayden¹, Hao Xu, K C Nicolaou, K N Houk.

Abstract

[reaction: see text] Quantum mechanical calculations demonstrate that the second step of a Claisen-Diels-Alder reaction cascade controls regioselectivity that gives advanced intermediates for the synthesis of gambogin and 1-O-methyllateriflorone.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 16805534 DOI： 10.1021/ol060917o

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

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Cited

7 in total

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Journal: Chemistry Date: 2010-09-03 Impact factor: 5.236

2. Theoretical study of the mechanism of highly diastereoselective formation of a strained 3-azabicyclo[3.2.0]heptane derivative.

Authors: Maryam Nemati; Nematollah Arshadi
Journal: J Mol Model Date: 2015-03-14 Impact factor: 1.810

3. Pericyclic cascade with chirality transfer: reaction pathway and origin of enantioselectivity of the hetero-Claisen approach to oxindoles.

Authors: Nihan Çelebi-Ölçüm; Yu-hong Lam; Edward Richmond; Kenneth B Ling; Andrew D Smith; Kendall N Houk
Journal: Angew Chem Int Ed Engl Date: 2011-10-04 Impact factor: 15.336

Origins of selectivity in pericyclic reaction cascades for the synthesis of gambogin and lateriflorone.

Review 1. Chemistry and biology of the caged Garcinia xanthones.

2. Theoretical study of the mechanism of highly diastereoselective formation of a strained 3-azabicyclo[3.2.0]heptane derivative.

3. Pericyclic cascade with chirality transfer: reaction pathway and origin of enantioselectivity of the hetero-Claisen approach to oxindoles.

Review 4. Dearomatization strategies in the synthesis of complex natural products.

5. Absolute configuration of (-)-gambogic acid, an antitumor agent.

6. Evaluation of the pharmacophoric motif of the caged Garcinia xanthones.

7. A-ring oxygenation modulates the chemistry and bioactivity of caged Garcinia xanthones.