Total synthesis and biological evaluation of tyroscherin

Organic Letters

Volumn 12, Issue 19, 2010, Pages 4308-4311

  Tae, Hyun Seop ^a   Hines, John ^a   Schneekloth, Ashley R ^a   Crews, Craig M ^a,b  

^a YALE UNIVERSITY   (United States)

^b YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADRENALIN; DRUG DERIVATIVE; FATTY ALCOHOL; TYROSCHERIN;

ARTICLE; CHEMICAL STRUCTURE; HUMAN; IC 50; STEREOISOMERISM; SYNTHESIS; TUMOR CELL LINE;

CELL LINE, TUMOR; EPINEPHRINE; FATTY ALCOHOLS; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77957113894     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101801u     Document Type: Article

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31. This protecting group on the C3 alcohol had an important influence on the selectivity and yield of the cross metathesis reaction. The best E: Z ratio was obtained with the C3 acetate compared to other esters or the free hydroxyl.
32. D = +7.8 (c 0.330, MeOH). The large discrepancy in optical rotation values is perhaps due to the equivalent of amine salt in C2.
33. The syntheses of 8 key fragments and 16 stereoisomers and the biological results will be reported elsewhere.
34. For more details on the syntheses of 19, 20, 21, and 3, see Supporting Information.