Synthesis of (2S,3S,8S,9S)-Adda from D-glucose

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5645-5648

  Sin, Ny ^a   Kallmerten, James ^a  

^a SYRACUSE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 2,6,8 TRIMETHYL 10 PHENYL 4,6 DECADIENOIC ACID; AMINO ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS;

EID: 0030570910     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01217-8     Document Type: Article

References (27)

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20. 13C NMR spectroscopy. Satisfactory combustion and/or HRMS analyses were obtained for all new compounds.
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22. 12. Such a mechanism is consistent with our stereochemical assignment for 13, which is based on the H3-H4 coupling constant of 7.2 Hz indicative of a cis relationship between the C3 and C4 substituent. An alternative mechanism, involving [1,2] migration of the C2-C3 bond of 11b with concomittant displacement of the C4 hydroxyl, would yield the C3 epimer of 13. Studies aimed at defining the scope and mechanism of this unusual pyranose rearrangement are in progress.
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27. 15. The 500 MHz NMR, IR and FAB low resolution mass spectra of 17 corresponded to spectra of authentic material kindly provided by Prof. Rinehart.