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PMID: 19603820 Published · ppublish English Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't

Exploring symmetry-based logic for a synthesis of palau'amine.

The Journal of organic chemistry ·Vol. 74 ·No. 16 ·2009-08-21 ·Pages 5909-19

Li Q, Hurley P, Ding H, Roberts AG, Akella R, Harran PG

Abstract

A synthetic approach to palau'amine is described that exploits veiled symmetry in the structure. Bis-alkylidenes i have been prepared and found susceptible to halogenative desymmetrization using t-BuOCl. This oxidation forms the imbedded spirocyclopentane motif observed in the natural product. A host of atypical reactions and processes developed during these studies are discussed, as are plans for completing total syntheses of this compound class.

MeSH Terms

Alkaloids/chemistry Cyclization Dimerization Guanidines/chemical synthesis,chemistry Reproducibility of Results Spiro Compounds/chemical synthesis,chemistry Stereoisomerism Substrate Specificity

Chemicals

Alkaloids Guanidines Spiro Compounds palau'amine

Authors & Affiliations

6 authors, click to expand affiliations / ORCID

Li Qingyi

Department of Biochemistry, University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, USA.

Hurley Paul

Ding Hui

Roberts Andrew G

Akella Radha

Harran Patrick G

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23 references, click to expand

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Article Info

Journal

The Journal of organic chemistry

Abbr.

J Org Chem

ISSN

1520-6904

DOI

10.1021/jo900755r

Published

2009-08-21

Pages

5909-19

Language

English

Region

United States

NLM ID

2985193R

PMCID

PMC2888864

Subset

Grants

NIGMS NIH HHS · R01 GM060591 · United States

NIGMS NIH HHS · R01 GM060591-09 · United States

NIGMS NIH HHS · R01-GM60591 · United States

External Links

PubMed source DOI: 10.1021/jo900755r PMC Full Text View journal details

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Exploring symmetry-based logic for a synthesis of palau'amine.

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