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The sulfinyl moiety as an internal nucleophile. Part 8: Efficient, stereospecific synthesis of (+)-polyoxamic acid

โœ Scribed by Sadagopan Raghavan; Suju C. Joseph

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
221 KB
Volume
44
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A straightforward and stereospecific synthesis of (+)-polyoxamic acid is disclosed. The key step of the synthesis involves the regio-and stereospecific bromohydration of an olefin via intramolecular participation by the sulfinyl group.

๐Ÿ“œ SIMILAR VOLUMES

Sulfinyl moiety as an internal nucleophi
Sulfinyl moiety as an internal nucleophile. Part 6: Stereospecific synthesis of 3-amino-2-hydroxy-4-phenylbutanoate
โœ Sadagopan Raghavan; M.Abdul Rasheed ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 157 KB

A novel and stereospecific synthesis of (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoate (AHPBA) is disclosed. The key step includes regio-and stereospecific functionalization of an alkene by the pendant sulfinyl group.

The sulfinyl moiety as an intramolecular
The sulfinyl moiety as an intramolecular nucleophile. Part 3: Synthesis of (โˆ’)-muricatacin
โœ Sadagopan Raghavan; S.C. Joseph ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 208 KB

A short, efficient and highly stereoselective synthesis of (-)-(R,R)-muricatacin is reported. The key steps include a highly diastereoselective reduction of a b-ketosulfoxide to a b-hydroxy sulfoxide, regio-and stereoselective bromohydration of an olefin employing the sulfinyl group as an internal n