A Route to Glycals in the Allal and Gulal Series: Synthesis of the Thiosugar of Esperamicin A1

Journal of Organic Chemistry

Volumn 55, Issue 7, 1990, Pages 1979-1981

  Wittman, Mark D ^a   Halcomb, Randall L ^a   Danishefsky, Samuel J ^a   Golik, Jerzy ^b   Vyas, Dolatrai ^b  

^a YALE UNIVERSITY   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESPERAMICIN A1;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN;

EID: 0025167104     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00294a004     Document Type: Article

References (39)

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24. All new compounds were characterized by IR and NMR spectroscopy, HRMS, and optical rotation.
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31. A problem with the simple acetoxonium mechanism is that glycal formation is not noted until thiophile12 (either secondary amine or phosphite) is added.
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39. The absolute configuration of 3 has also been determined by single-crystal X-ray analysis of its p-bromobenzoate: Golik, J.; Clardy, J. Unpublished results.