Based on the consideration that biologically active chiral compounds should be prepared
in optically active forms showing desired biological activities, the compounds not
only exhibiting interesting biological activities but also bearing intriguing structures
were selected as synthetic targets and their efficient syntheses were studied by
employing optical resolution, asymmetric synthesis, and chemical transformation.
Thus, efficient syntheses of anticancer agents such as anthracyclines, nogalamycins,
and sesbanimides were accomplished in optically active forms. Syntheses of optically
active quinocarcin and fredericamycin A showing pronounced anticancer activities
were also studied. A number of efficient synthetic routes to the optically active
key intermediates of carbapenem antibiotics and antihypertensive peptide-like renin
inhibitors were successfully explored. 1. Introduction 2. Synthetic Studies on Optically
Active Anthracyclines 2.1. Synthesis of 4-Demethoxyanthracyclinones 2.2. Synthesis
of an L-Daunosamine Derivative 2.3. Synthesis of 4-Demethoxyanthracyclines 2.4.
Synthesis of Anthracycline Congeners 3. Synthetic Studies on Optically Active Nogalamycin
Congeners 3.1. Synthesis of the CDEF-Ring 3.2. Synthesis of Nogalamycin Congeners
3.3. Structure-Activity Relationships of Nogalamycin Congeners 4. Synthetic Studies
on Optically Active Sesbanimides 4.1. Synthesis of Sesbanimide A and B 4.2. Synthesis
and Structure-Activity Relationships of Sesbanimide Congeners 5. Synthetic Studies
on Optically Active Quinocarcin 6. Synthetic Studies on Optically Active Fredericamycin
A 7. Synthetic Studies on Optically Active Carbapenem Key Intermediates 7.1. Synthesis
by the Cycloaddition Reaction of a Nitrone 7.2. Synthesis by the [2 + 2] Cycloaddition
Reactions 7.3. Synthesis by the Reformatsky Reaction 8. Synthetic Studies on the
Key Intermediates of Peptide-Like Renin Inhibitors 8.1. Synthesis by the 1,2-Addition
Reactions with Aldehydes 8.2. Synthesis by the 1,2-Addition Reaction with an Imine
8.3. Synthesis by the [2 + 2] Cycloaddition Reaction 8.4. Synthesis Employing Optical
Resolution, Asymmetric Reduction, and Chemoselective Amidation 9. Conclusion
