The Role of Total Synthesis in Structure …
27
Table 1
Summary of total synthesis-based structure elucidation of stagonolides A–K
Entry
Stagonolide
Status of structure elucidation after
total synthesis
Confirmed or revised structure
based on synthesis
Source of chirality in total syntheses Ref.
1
Stagonolide A (85)
Constitution and relative
configuration trans
confirmed;
confirmation of absolute
configuration pending
d-Ribose
[92]
2
d-Ribose
[93]
3
d-Glucose
[94]
4
Chiral auxiliary mediated aldol
addition
[95]
5
Stagonolide B (86)
Fully confirmed
d-Ribose
[100]
6
d-Ribose; Co-salen cat. kinetic
resolution
[101]
7
d-Ribose; lipase-cat. kinetic
resolution
[93]
8
Enzymatic hydrocyanation;
asymmetric dihydroxylation
[28]
9
Stagonolide C (83)
Fully confirmed
l-Malic acid; Sharpless epoxidation [86]
10
Lipase- and Ru-cat. dynamic kinetic
resolution
[102]
11
d-Mannitol
[103]
12
l-Diethyl tartrate
[104]
13
d-Mannitol; Sharpless kinetic
resolution
[105]
(continued)