Journal
TETRAHEDRON
Volume 67, Issue 35, Pages 6497-6512Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.06.008
Keywords
Studies on the synthesis of tetrafibricin; Double allylboration; Allene hydroboration; Kinetically controlled; Tetrabutylammonium allenyltrifluoroborate; Stereoselective synthesis of syn-1,5-E-diols
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Funding
- National Institutes of Health [GM038436]
- German Academic Exchange Service (DAAD)
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Interest in the synthesis of the C(23) C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42, and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% ee), diastereoselectivity (dr >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23) C(40) fragment 2 of tetrafibricin. (C) 2011 Elsevier Ltd. All rights reserved.
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