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

Abstract : The relative configuration of tulearin A I (R3 = H, R8 = CONH2, R9 = H) was detd. by X-ray diffraction anal. of a cyclic carbonate deriv. I (R3 = H, R8R9 = CO), and the abs. configuration (2R,3R,5S,8S,9S,15R,17S) from the 9-MTPA-esters I [R3 = H, R8 = CONH2, R9 = COC(OMe)(CF3)Ph-(R), -(S)] was detd. using the modified Mosher's method. A mechanism for the unexpected formation of the cyclic carbonate was suggested. Two N-phenyltriazolinedione cycloadducts of tulearin A were also prepd. Two addnl. tulearins, B and C I (R3 = CONH2, R8 = CONH2, R9 = H; R3 = H, R8 = H, R9 = H, resp.), were isolated in very small amts. from Fascaplysinopsis, and their structures are elucidated by spectroscopic means. [on SciFinder(R)]
Type de document :
Article dans une revue
Tetrahedron Letters, Elsevier, 2009, 50 (27), pp.3820--3822. 〈10.1016/j.tetlet.2009.04.028〉
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http://hal.univ-reunion.fr/hal-01188142
Contributeur : Claire Tessier <>
Soumis le : vendredi 28 août 2015 - 15:07:57
Dernière modification le : vendredi 14 septembre 2018 - 08:16:16

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Ashgan Bishara, Amira Rudi, Israel Goldberg, Maurice Aknin, Yoel Kashman. Tulearins A, B, and C; structures and absolute configurations. Tetrahedron Letters, Elsevier, 2009, 50 (27), pp.3820--3822. 〈10.1016/j.tetlet.2009.04.028〉. 〈hal-01188142〉

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