TY - JOUR
T1 - Tulearins A, B, and C; structures and absolute configurations
AU - Bishara, Ashgan
AU - Rudi, Amira
AU - Goldberg, Israel
AU - Aknin, Maurice
AU - Kashman, Yoel
PY - 2009/7/8
Y1 - 2009/7/8
N2 - The relative configuration of tulearin A (1) is determined by X-ray diffraction analysis of a cyclic carbonate derivative 2 and the absolute configuration (2R,3R,5S,8S,9S,15R,17S) from the 9-MTPA-esters 1R and 1S 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.
AB - The relative configuration of tulearin A (1) is determined by X-ray diffraction analysis of a cyclic carbonate derivative 2 and the absolute configuration (2R,3R,5S,8S,9S,15R,17S) from the 9-MTPA-esters 1R and 1S 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.
UR - http://www.scopus.com/inward/record.url?scp=65549167779&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2009.04.028
DO - 10.1016/j.tetlet.2009.04.028
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AN - SCOPUS:65549167779
SN - 0040-4039
VL - 50
SP - 3820
EP - 3822
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 27
ER -