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. 2016 Jul 8;21(7):892. doi: 10.3390/molecules21070892

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© 2016 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).

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Scheme 5 — Total synthesis of subunits A, B, and C of (+)-discodermolide (29). Reagents and conditions: (a) (1) t-BuLi, Me₂CuLi, LiCN, Et₂O/DMS then n-Bu₃SnCl; (2) TEMPO, BAIB; (b) (1) TBSOTf, 2,6-lutidine, O₃, Sudan III then DMS; (2) TBSOTf, 2,6-lutidine; (3) Ni(acac)₂, (CH₂=CH₄)Sn, MeLi; (4) DDQ, CH₂Cl₂/H₂O, I₂, PPh₃; (c) (1) TBSCl, imidazole, DIBAL-H, CH₂Cl₂, (COCl)₂, DMSO; (2) O₃, Sudan III, (EtO)₂P(O)CH₂C(O)NMe, NaH; (3) PhCHO, KHMDS.

Scheme 5 — Total synthesis of subunits A, B, and C of (+)-discodermolide (29). Reagents and conditions: (a) (1) t-BuLi, Me₂CuLi, LiCN, Et₂O/DMS then n-Bu₃SnCl; (2) TEMPO, BAIB; (b) (1) TBSOTf, 2,6-lutidine, O₃, Sudan III then DMS; (2) TBSOTf, 2,6-lutidine; (3) Ni(acac)₂, (CH₂=CH₄)Sn, MeLi; (4) DDQ, CH₂Cl₂/H₂O, I₂, PPh₃; (c) (1) TBSCl, imidazole, DIBAL-H, CH₂Cl₂, (COCl)₂, DMSO; (2) O₃, Sudan III, (EtO)₂P(O)CH₂C(O)NMe, NaH; (3) PhCHO, KHMDS.