Total Synthesis of the Potent HIF-1 Inhibitory Antitumor Natural Product, (8<i>R</i>)-Mycothiazole, via Baldwin–Lee CsF/CuI sp<sup>3</sup>–sp<sup>2</sup>-Stille Cross-Coupling. Confirmation of the Crews Reassignment
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04/09/2015
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| Resumo |
A convenient asymmetric total synthesis of the potent HIF-1 inhibitory antitumor natural product, (−)- or (+)-(8<i>R</i>)-mycothiazole (<b>1</b>), is described. Not only does our synthesis confirm the 2006 structural reassignment made by Crews (Crews, P., et al. <i>J. Nat. Prod</i>. <b>2006</b>, <i>69</i>, 145), it revises the [α]<sub>D</sub> data previously reported for this molecule in MeOH from −13.7° to +42.3°. The newly developed route to (8<i>R</i>)-<b>1</b> sets the C(8)–OH stereocenter via Sharpless AE/2,3-epoxy alcohol reductive ring opening and utilizes two Baldwin–Lee CsF/cat. CuI Stille cross-coupling reactions with vinylstannanes <b>8</b> and <b>3</b> to efficiently elaborate the C(1)–C(4) and C(14)–C(18) sectors. |
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| Idioma(s) |
eng |
| Direitos |
info:eu-repo/semantics/restrictedAccess |
| Fonte |
Wang , L & Hale , K J 2015 , ' Total Synthesis of the Potent HIF-1 Inhibitory Antitumor Natural Product, (8 R )-Mycothiazole, via Baldwin–Lee CsF/CuI sp 3 –sp 2 -Stille Cross-Coupling. Confirmation of the Crews Reassignment ' Organic Letters , vol 17 , no. 17 , pp. 4200–4203 . DOI: 10.1021/acs.orglett.5b01966 |
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article |
