ISSN:
0947-6539
Keywords:
natural products
;
swinholide A
;
total syntheses
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The total synthesis of 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 prewinholide A methyl ester (7), preswinholide A (8), and hemiswinholide A (78).
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.1460020716
