In:
Chemistry – An Asian Journal, Wiley, Vol. 11, No. 9 ( 2016-05-06), p. 1425-1435
Kurzfassung:
Two independent synthetic approaches were evaluated for the final phase of the asymmetric total synthesis of propindilactone G ( 1 ). The key steps that led to the completion of the asymmetric total synthesis included: 1) an intermolecular oxidative heterocoupling reaction of enolsilanes to link the core structure to the side chain; 2) an intermolecular Wittig reaction for the formation of the α,β,γ,δ‐unsaturated ester; and 3) a regio‐ and stereoselective OsO 4 ‐catalyzed dihydroxylation of an α,β,γ,δ‐unsaturated enone, followed by an intramolecular lactonization reaction to afford the final product. These reactions enabled the synthesis of (+)‐propindilactone G in only 20 steps. As a consequence of our synthetic studies, the structure of (+)‐propindilactone G has been revised. Furthermore, the direct oxidative coupling strategy for ligation of the core of propindilactone G with its side chain may find application in the syntheses of other natural products and complex molecules.
Materialart:
Online-Ressource
ISSN:
1861-4728
,
1861-471X
DOI:
10.1002/asia.201600131
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2016
ZDB Id:
2233006-9
