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

Hitomi Yamada, Masaatsu Adachi, Toshio Nishikawa

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

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.

Original language	English
Pages (from-to)	11221-11223
Number of pages	3
Journal	Chemical Communications
Volume	49
Issue number	95
DOIs	https://doi.org/10.1039/c3cc46949b
Publication status	Published - 2013 Nov 5
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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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.",

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