A stereospecific elimination to form dehydroamino acids: Synthesis of the phomopsin tripeptide side chain

Journal of the American Chemical Society

Volumn 121, Issue 25, 1999, Pages 6100-6101

  Stohlmeyer, Michelle M ^a   Tanaka, Hiroko ^a   Wandless, Thomas J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA,BETA DEHYDROAMINO ACID; AMINO ACID; PHENYLALANINE DERIVATIVE; PHOMOPSIN A; PHOSPHATASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHLORINATION; CHROMATOGRAPHY; DEHYDRATION; DIASTEREOISOMER; ENANTIOMER; ENZYME INHIBITION; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033618118     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991037q     Document Type: Article

References (23)

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21. Bases other than DBU have been used for the two-step procedure with similar success. Tetramethylguanidine, 1,5-diazabicyclo[4,3,0]non-5-ene, and potassium tert-butoxide efficiently convert sulfamidites to the corresponding alkenes (data not shown).
22. 4 to form the cyclic sulfamidate, which stereoselectively provides the desired product upon treatment with DBU.
23. Treatment of Cbz-serine-benzyl ester with thionyl chloride using the one-step procedure provided 74% yield of the α,β-dehydroamino ester.