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Literature DB >> 11772104

Total synthesis of epi-7-deoxypancratistatin via aza-Payne rearrangement and intramolecular cyclization.

Uwe Rinner¹, Peter Siengalewicz, Tomas Hudlicky.

Abstract

[reaction: see text] epi-7-Deoxypancratistatin containing the cis-fused phenanthridone core was synthesized in 12 steps from bromobenzene. Key features of this synthesis include the enzymatic oxidation of bromobenzene with toluene dioxygenase, selective opening of a cyclic sulfate over an aziridine with oxygen nucleophiles, and an intramolecular Lewis acid-catalyzed cyclization onto an epoxy conduramine derived via aza-Payne rearrangement.

Entities: Chemical

Mesh：

Substances：

Year: 2002 PMID： 11772104 DOI： 10.1021/ol0169877

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

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Cited

9 in total

1. Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.

Authors: Jonathan Collins; Uwe Rinner; Michael Moser; Tomas Hudlicky; Ion Ghiviriga; Anntherese E Romero; Alexander Kornienko; Dennis Ma; Carly Griffin; Siyaram Pandey
Journal: J Org Chem Date: 2010-05-07 Impact factor: 4.354

Total synthesis of epi-7-deoxypancratistatin via aza-Payne rearrangement and intramolecular cyclization.

1. Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.

2. Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation.

Review 3. Chemistry, biology, and medicinal potential of narciclasine and its congeners.

4. Unnatural C-1 homologues of pancratistatin - Synthesis and promising biological activities.

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 and biological evaluation of unnatural derivatives of narciclasine: 7-aza-nornarciclasine and its N-oxide.

Review 9. The role of biocatalysis in the asymmetric synthesis of alkaloids.