Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates

1.1 Hydroxymethylpyrrolidines.

2-Hydroxymethyl-pyrrolidines.

Dihydro-2-hydroxymethylpyrrole (Nectrisine).

2,5-Dihydroxymethyl-pyrrolidines.

1.2 2-Carboxypyrrolidines.

Hydroxyprolines.

Bulgecins.

1.3 2-Aralkyl pyrrolidines.

Anisomycin.

Preussin.

1.4 2-Aryl pyrrolidines.

Codonopsinine and Codonopsine.

1.5 Miscellaneous.

Detoxins.

Gualamycin.

Lactacystin.

Chapter 2 Five Membered Heterocycles with two Heteroatoms.

2.1 Hydantocidin.

2.2 Bleomycin.

2.3 Calyculins.

2.4 Acivicin.

2.5 Bengazole.

Chapter 3 Six Membered Nitrogen Heterocycles.

3.1 Hydroxymethylpiperidines.

Nojirimycin.

Mannojirimycin.

Galactonojirimycin.

Fagomine.

Homojirimycins.

3.2 Miscellaneous substituted piperidines.

2,6-Disubstituted-3-hydroxypiperidines.

Hydroxylated pipicolic acid.

Sesbanimide.

Siastatin.

Meroquinene.

Pyridyl of pyridomycin.

Chapter 4 Seven Membered Nitrogen Heterocycles.

4.1 Bengamides.

4.2 Liposidomycins.

Chapter 5 Fused Nitrogen Heterocycles.

5.1 3:5-Fused Heterocycles.

Azinomycins.

5.2 4:5-Fused Heterocycles.

b-Lactams.

5.3 5:5-Fused Heterocycles.

Polyhydroxypyrrolizidines.

Trehazolin.

Allosamidin.

Biotin.

5.4 5:6-Fused Heterocycles.

Hydroxylated indolizidines.

Castanospermine.

Swainsonine.

Lentiginosine.

Slaframine.

Miscellaneous.

Kifunensine.

Nagastatin.

Calystegines.

Mesembrine.

Streptolidine.

55 6:6-Fused Heterocycles.

Hydroxylated Quinuclidines.

Biopterins.

Isoquinolines.

Calycotomine.

Decumbenosine.

Laudanosine and glaucine.

Chapter 6 Multi-fused heterocycles.

6.1 Indoloquinolizidines.

Xylopinine.

Antirhine.

Allo-Yohimbane.

Ajmalicine.

6.2 Indolocarbazole Alkaloids.

6.3 Phenanthridone alkaloids.

6.4 Ecteinascidins