Kang Hyun Jung. Introduction. Leucascandrolide A ( 1 , Scheme 1) was isolated in 1996 from the calcareous sponge Leucascandra caveolata , collected off the east coast of New Caledonia, by Pietra and co-workers.
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Kang Hyun Jung
Leucascandrolide A (1, Scheme 1) was isolated in 1996 from the calcareous sponge Leucascandra caveolata,
collected off the east coast of New Caledonia, by Pietra and co-workers.
- This polyoxygenated 18-membered macrolide features two trisubstituted tetrahydropyran rings, one of
which has an unusual oxazole-bearing unsaturated side chain.
- Biological studies revealed potent cytotoxic activity against a range of cancer cell lines (IC50¼0.05 and
0.25 mgmL1 against KB oral epidermoid carcinoma and P388 leukemia cell lines, respectively), as well
as pronounced antifungal activity.
Preparation of Advanced Intermediate 18
Jacobson Asymmetric Hetero Diels-Alder Reaction 
HgII-Mediated Hydration of Alkyne 
- Alkynes are less basic than alkenes, Hg(OAc)2 (Hg+2 is a Lewis acid) is added to ensure complete reaction
1,5-Anti Stereoindution in the Boron-Mediated Aldol Reaction
Org. Lett.,4, 4325-4328, 2002
1,3-Anti Reduction of β-Hydroxy Ketone
J. Am. Chem. Soc., 110, 11, 3560-3578, 1988
Selective Iodine(III)/TEMPO-Mediated Oxidation 
J. Org. Chem., 62, 6974-6977, 1997
Elaboration to the Macrocyclic Core 24
DIBAL Reduction and in situ Acetylation 
J. Org. Chem., 61, 8317-8320, 1996
1,3-Asymmetric redution 
Mistunobu Macrolactonization (Esterification)
Synthesis, 1, 1981
Preparation of the Oxazole-bearing Side Chain 3
α-Alkylation of Hydrazone and Alkyl halide 
Sonogashira Coupling of Functionalized Trifloyl Oxazole 
Org. Lett.,4, 2485-2488, 2002
Completion of the Total Synthesis of Leucascandrolide A
Lindlar Hydrogenation