28
B. Schmidt
Table 1
(continued)
Entry
Stagonolide
Status of structure elucidation after
total synthesis
Confirmed or revised structure
based on synthesis
Source of chirality in total syntheses Ref.
14
Proline cat. aminooxylation;
Jorgensen epoxidation
[106]
15
d-Glyceraldehyde
[107]
16
Stagonolide D (98)
Originally assigned structure 87
was
revised to 98
(stereocenters are
(4S,7R,8S,9R)-configured)
Sharpless asymmetric epoxidation
(synthesis of originally assigned
structure and confirmation)
[108]
17
d-Mannitol (synthesis of originally
assigned structure and confirmation)
[109]
18
d-Xylose (synthesis of
ent-stagonolide
D; revision of
configuration to (4S,7R,8S,9R)
proposed)
[98]
19
(R)-Glycidol; alpine-borane
carbonyl reduction (synthesis of
stagonolide D; revised absolute and
relative configuration confirmed
[110]
20
Stagonolide E (88)
Fully confirmed
Co-salen cat. kinetic resolution;
Sharpless epoxidation
[111]
21
Lipase-cat. kinetic resolution;
asymmetric LAH-binol carbonyl
reduction
[112]
22
d-Mannitol; lipase-Ru-catalyzed
dynamic kinetic resolution
[66]
(continued)