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Beilstein J. Org. Chem. 2012, 8, 1287–1292, doi:10.3762/bjoc.8.146
Graphical Abstract
Figure 1: Pheromone spiroketals.
Figure 2: Reported structures of the cephalosporolides and penisporolides.
Scheme 1: Stereocontrol of oxygenated 5,5-spiroketals.
Scheme 2: Synthesis of the reported cephalosporolide H and its spiro isomer.
Scheme 3: Synthesis of the reported C9-epi-cephalosporolide H and its spiro isomer.
Figure 3: Reported and synthesized cephalosporolide H isomers.
Scheme 4: Synthesis of homopropargyl silyl ether.
Scheme 5: Synthesis of cephalosporolide E.
Beilstein J. Org. Chem. 2011, 7, 570–577, doi:10.3762/bjoc.7.66
Figure 1: Common spiroketal motifs.
Figure 2: Spiroketal-containing cephalosporolide natural products.
Scheme 1: Cyclocondensation vs. cycloisomerization for the synthesis of spiroketals.
Scheme 2: Retrosynthetic analysis of cephalosporolide H.
Scheme 3: Key precedents for the desired cycloisomerization.
Scheme 4: Proposed cycloisomerization with acetal hydrolysis.
Scheme 5: Synthesis of model cyclization substrate 13.
Scheme 6: Synthesis of reported structure of cephalosporolide H.
Scheme 7: Proposed mechanism.
Scheme 8: Control experiment for gold-activation of the alkyne.
Beilstein J. Org. Chem. 2008, 4, No. 44, doi:10.3762/bjoc.4.44
Figure 1: Benzyl bromide, benzyl trichloroacetimidate, and 2-benzyloxy-1-methylpyridinium triflate (1).
Scheme 1: Published syntheses of benzyl esters from alcohols using neutral reagent 1; other benzylation proce...
Scheme 2: Preparation of 2-benzyloxypyridine (2).
Scheme 3: Synthesis of a benzyl ester from a carboxylic acid.
Scheme 4: Representative synthesis of a halobenzyl ether under neutral conditions.