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

Hitomi Yamada; Masaatsu Adachi; Toshio Nishikawa

doi:10.1039/c3cc46949b

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

Chem Commun (Camb). 2013 Dec 11;49(95):11221-3. doi: 10.1039/c3cc46949b. Epub 2013 Oct 23.

Authors

Hitomi Yamada¹, Masaatsu Adachi, Toshio Nishikawa

Affiliation

¹ Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan. nisikawa@agr.nagoya-u.ac.jp.

PMID: 24150697
DOI: 10.1039/c3cc46949b

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds / chemistry*
Dicarboxylic Acids / chemical synthesis
Dicarboxylic Acids / chemistry*
Galactose / analogs & derivatives
Galactose / chemistry
Hydroxylation
Organophosphorus Compounds / chemical synthesis
Organophosphorus Compounds / chemistry*
Stereoisomerism

Substances

Bridged Bicyclo Compounds
Dicarboxylic Acids
Organophosphorus Compounds
bicyclo(3.3.1)nonane
galactal
tagetitoxin
Galactose