Tulearins A, B, and C; structures and absolute configurations

The relative configuration of tulearin A ( 1) is determined by X-ray diffraction analysis of a cyclic carbonate derivative 2 and the absolute configuration (2 R,3 R,5 S,8 S,9 S,15 R,17 S) from the 9-MTPA-esters 1 R and 1 S is determined using the modified Mosher’s method. A mechanism for the unexpec...

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Bibliographic Details
Published in:Tetrahedron letters 2009-07, Vol.50 (27), p.3820-3822
Main Authors: Bishara, Ashgan, Rudi, Amira, Goldberg, Israel, Aknin, Maurice, Kashman, Yoel
Format: Article
Language:English
Subjects:
Chemical Sciences
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Summary:The relative configuration of tulearin A ( 1) is determined by X-ray diffraction analysis of a cyclic carbonate derivative 2 and the absolute configuration (2 R,3 R,5 S,8 S,9 S,15 R,17 S) from the 9-MTPA-esters 1 R and 1 S is determined using the modified Mosher’s method. A mechanism for the unexpected formation of carbonate 2 is suggested. Two N-phenyltriazolinedione derivatives 3 and 4 are also prepared. Two additional tulearins, B and C ( 5 and 6) are isolated in very small amounts and their structures are elucidated by spectroscopic means.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.04.028