2003
DOI: 10.1016/s0040-4039(03)00110-2
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Stereoselective synthesis of C15C24 and C25C30 fragments of dolabelides

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Cited by 28 publications
(10 citation statements)
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“…Other structural features possessed by this family of macrolactones include 1,3- anti -diol fragments found at C7/C9 and C19/C21, along with an accompanying 1,3- syn -diol at C9/C11 and polypropionate fragments at C1/C4 and C21/C23. The stereochemical complexity and biological profile of this class of compounds has attracted synthetic interest from several groups 3 and in 2006, the first total synthesis of dolabelide D was reported by Leighton and coworkers. 4 …”
Section: Introduction: the Dolabelide Familymentioning
confidence: 99%
“…Other structural features possessed by this family of macrolactones include 1,3- anti -diol fragments found at C7/C9 and C19/C21, along with an accompanying 1,3- syn -diol at C9/C11 and polypropionate fragments at C1/C4 and C21/C23. The stereochemical complexity and biological profile of this class of compounds has attracted synthetic interest from several groups 3 and in 2006, the first total synthesis of dolabelide D was reported by Leighton and coworkers. 4 …”
Section: Introduction: the Dolabelide Familymentioning
confidence: 99%
“…A homologation reaction at the C(13) carbon would then deliver either the sulfonyl benzothiazole or the phosphonate at C (14). To our knowledge, although one synthetic approach of the C(16)-C(24) fragment of dolabelides 7 and two synthetic approaches of the C(15)-C(30) fragment 8,9 have been described, including one from our group, no synthesis of the C(1)-C( 14) portion of dolabelides has been reported so far. We describe herein a highly stereoselective synthesis of the C(1)-C(13) fragment of dolabelides using catalytic asymmetric hydrogenation 10,11 of b-keto esters and b-hydroxy ketone as a key step to install the C(3), C(7), C( 9) and C(11) hydroxyl-bearing stereocenters iteratively.…”
mentioning
confidence: 99%
“…Their structures were determined by HRFAB mass spectroscopy and 2D NMR, and their absolute configuration by the modified Mosher method [3]. Several groups have reported syntheses of Dolabelide fragments (C16-C24: [4], C15-C24 and C25-C30: [5], C15-C30: [6]). …”
mentioning
confidence: 99%