- Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation
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Diverse hydrogen-mediated C-C couplings enable construction of the actin-binding marine polyketide swinholide A in only 15 steps (longest linear sequence), roughly half the steps required in two prior total syntheses. The redox-economy, chemo- and stereos
- Shin, Inji,Hong, Suckchang,Krische, Michael J.
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supporting information
p. 14246 - 14249
(2016/11/13)
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- Total Synthesis of Swinholide A, Preswinholide A, and Hemiswinholide A
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The total synthesis of swinholide A (1) has been accomplished via key intermediate aldehyde 12 (Fig. 3), whose construction started from L-rhamnose (18), epoxide 21, and phenylsulfone orthoester 22, and proceeded through an Enders asymmetric alkylation (16 + 17 -> 15), a Ghosez cyclization (21 + 22 -> 20), and a Corey-Sharpless coupling reaction (13 + 14 -> 12).Elaboration of compound 12 along slightly different pathways culminated in the synthesis of carboxylic acid 10 and hydroxy compound 11, whose union by an esterification reaction, followed by ring closure of the subsequently derived hydroxy acid under Yamaguchi conditions, led to swinholide A (1) upon deprotection.The chemistry developed also allowed the total synthesis of preswinholide A methyl ester (7), preswinholide A (8), and hemiswinholide A (78).Keywords: natural products; swinholide A; total syntheses
- Nicolaou, K. C.,Patron, A. P.,Ajito, K.,Richter, P. K.,Khatuya, H.,et al.
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p. 847 - 868
(2007/10/03)
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- The total synthesis of swinholide A. Part 4: Synthesis of swinholide A and isoswinholide A from the protected monomeric seco acid, pre-swinholide A
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Swinholide A and isoswinholide A were synthesized in 7 steps from the fully protected seco acid 4. Key steps include: (i) bimolecular acylation, 7 + 10 → 12, (ii) selective hydrolysis of the methyl ester, 16 → 17, and (iii) regioselective macrolactonisati
- Paterson, Ian,Yeung, Kap-Sun,Ward, Richard A.,Smith, Julian D.,Cuimming, John G.,Lamboley, Serge
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p. 9467 - 9486
(2007/10/02)
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