STEREOCONVERGENT SYNTHESIS OF (2S,3S,8S,9S,4E,6E)-N-BOC-ADDA STARTINGFROM (S)-SERINE AND (S)-PHENYLLACTIC ACID

Authors
DANIELLO F MANN A SCHOENFELDER A TADDEI M
Citation
F. Daniello et al., STEREOCONVERGENT SYNTHESIS OF (2S,3S,8S,9S,4E,6E)-N-BOC-ADDA STARTINGFROM (S)-SERINE AND (S)-PHENYLLACTIC ACID, Tetrahedron, 53(4), 1997, pp. 1447-1456
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
4
Year of publication
1997
Pages
1447 - 1456
Database
ISI
SICI code
0040-4020(1997)53:4<1447:SSO(S>2.0.ZU;2-Q
Abstract
The important naturally occurring beta-amino acid N-Boc-ADDA is prepar ed following a disconnection of the C-C bond between the two E,E doubl e bonds. The stereochemistry of the two synthons was controlled using the alkylation of chiral bromoalienes derived from naturally occurring (S)-serine and (S)-phenyllactic acid. The cupration of bromoallenes d erived from (S)-serine also provides a general method for the synthesi s of chiral beta-alkylated aspartic acid derivatives. (C) 1997, Elsevi er Science Ltd.