Issue 95, 2013

Stereocontrolled synthesis of the oxathiabicyclo[3.3.1]nonane core structure of tagetitoxin

Abstract

Tagetitoxin is an unusually densely functionalized natural product, consisting of an unprecedented oxathiabicyclo[3.3.1]nonane ring system possessing acetate, phosphate, amide, carboxylic acid, and amine groups with six contiguous asymmetric centers. A fully functionalized core structure of tagetitoxin was synthesized from tri-O-acetyl-D-galactal in a highly stereoselective manner.

Graphical abstract: Stereocontrolled synthesis of the oxathiabicyclo[3.3.1]nonane core structure of tagetitoxin

Supplementary files

Article information

Article type
Communication
Submitted
11 Sep 2013
Accepted
09 Oct 2013
First published
10 Oct 2013

Chem. Commun., 2013,49, 11221-11223

Stereocontrolled synthesis of the oxathiabicyclo[3.3.1]nonane core structure of tagetitoxin

H. Yamada, M. Adachi and T. Nishikawa, Chem. Commun., 2013, 49, 11221 DOI: 10.1039/C3CC46949B

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