95927-67-6Relevant articles and documents
Total Synthesis of Swinholide A
Nicolaou, K. C.,Ajito, K.,Patron, A. P.,Khatuya, H.,Richter, P. K.,Bertinato, P.
, p. 3059 - 3060 (1996)
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Total Synthesis of Swinholide A, Preswinholide A, and Hemiswinholide A
Nicolaou, K. C.,Patron, A. P.,Ajito, K.,Richter, P. K.,Khatuya, H.,et al.
, p. 847 - 868 (2007/10/03)
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
Total synthesis of swinholide A and hemiswinholide A
Paterson, Ian,Yeung, Kap-Sun,Ward, Richard A.,Cumming, John G.,Smith, Julian D.
, p. 9391 - 9392 (2007/10/02)
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