Synthesis Of Naturally Occurring Nitrogen Heterocycles From Carbohydrates

by El Ashry, El Sayed H.; El Nemr, Ahmed
Edition: 1st
Format: Hardcover
Pub. Date: 2005-05-27
Publisher(s): Wiley-Blackwell
List Price: $377.32

Buy New

Usually Ships in 3-4 Business Days
$359.35

Rent Textbook

Select for Price
There was a problem. Please try again later.

Used Textbook

We're Sorry
Sold Out

eTextbook

We're Sorry
Not Available

How Marketplace Works:

  • This item is offered by an independent seller and not shipped from our warehouse
  • Item details like edition and cover design may differ from our description; see seller's comments before ordering.
  • Sellers much confirm and ship within two business days; otherwise, the order will be cancelled and refunded.
  • Marketplace purchases cannot be returned to eCampus.com. Contact the seller directly for inquiries; if no response within two days, contact customer service.
  • Additional shipping costs apply to Marketplace purchases. Review shipping costs at checkout.

Summary

Carbohydrates are widely distributed in nature and widely available, and so are considered as a promising feedstock for the preparation of many organic chemical compounds. They are particularly useful in the preparation of nitrogen heterocycles because of their related structural characteristics and easy availability.Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates will review the recent literature dealing with use of carbohydrates as raw materials in the synthesis of these materials. The text contains six chapters arranged according to the complexity of the heterocyclic compounds discussed, ranging from five to seven membered rings and from single to multiple fused rings. The book provides a detailed discussion of the various synthetic approaches to these compounds, using carbohydrate starting materials, and does not merely reference synthetic methodology but attempts to give as much detail as possible on the actual experimental conditions used, in such a way that the chemist can use the information directly to design a multi-step synthesis. It discusses the different approaches to the synthesis of a wide range of naturally occurring nitrogen heterocycles in a format that enables the reader to make comparisons and decisions on whether to use a certain procedure, to modify it, or to devise a new synthetic methodology.

Author Biography

Professor El Sayed H. El Ashry1 Dr. Ahmed El Nemr 2

1 Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, Egypt.

2 Environmental Division, National Institute of Oceanography and Fisheries, Kayet Bay, Alexandria, Egypt.

Table of Contents

Preface ix
Author details x
List of abbreviations and acronyms used in this book
xi
Introduction xiv
Five-membered nitrogen heterocycles
1(74)
Hydroxymethylpyrrolidines
1(29)
2-Hydroxymethylpyrrolidines
1(1)
Synthesis from D-glucose
2(1)
Synthesis from D-mannose
3(1)
Synthesis from L-arabinose
3(1)
Synthesis from D-xylose
4(2)
Synthesis from D-threose
6(1)
Synthesis from D-lyxonolactone
7(1)
Synthesis from D-gulonolactone
7(4)
Dihydro-2-hydroxymethylpyrrole (nectrisine)
11(1)
Synthesis from D-glucose
11(1)
Synthesis from D-arabinose
12(1)
Synthesis from D-glyceraldehyde
13(1)
Synthesis from L-threitol
14(2)
2,5-Dihydroxymethylpyrrolidines
16(1)
Synthesis from D-glucose
16(2)
Synthesis from D-glucosamine
18(1)
Synthesis from D-fructose
18(1)
Synthesis from L-sorbose
18(3)
Synthesis from D-arabinose
21(1)
Synthesis from L-xylose
22(1)
Synthesis from D-iditol
22(1)
Synthesis from D-mannitol
23(2)
Synthesis from D-glucosamic acid
25(1)
Synthesis from D-glyconolactone
25(5)
2-Carboxypyrrolidines
30(16)
Hydroxyprolines
30(1)
Synthesis from D-glucose
31(1)
Synthesis from D-mannitol
32(2)
Synthesis from L-arabinono- and L-lyxono-lactones
34(1)
Synthesis from D-ribonolactone
35(1)
Synthesis from D-gulonolactones
35(1)
Synthesis from D-gluconolactone
36(1)
Synthesis from D-glucoronolactone
36(2)
Synthesis from D-xylonolactone
38(3)
Bulgecins
41(1)
Synthesis from D-glucose
41(2)
Synthesis from D-glucuronolactone
43(3)
2-Aralkyl pyrrolidines
46(14)
(-)-Anisomycin
46(1)
Synthesis from D-galactose
46(1)
Synthesis from L-arabinose
46(2)
Synthesis from D-ribose
48(1)
Synthesis from L-threose
48(1)
Synthesis from L-threitol
48(4)
Synthesis from D-mannitol
52(4)
(+)-Preussin
56(1)
Synthesis from D-glucose
56(1)
Synthesis from D-mannose
57(1)
Synthesis from D-arabinose
58(2)
2-Aryl pyrrolidines
60(4)
Codonopsinine and codonopsine
60(4)
Miscellaneous
64(11)
Detoxins
64(1)
Synthesis from D-glucose
65(2)
Synthesis from L-ascorbic acid
67(3)
Gualamycin
70(2)
Lactacystin
72(3)
Five-membered heterocycles with two heteroatoms
75(30)
(+)-Hydantocidin
75(11)
Synthesis from D-fructose
76(4)
Synthesis from D-ribose
80(2)
Synthesis from D-threose
82(1)
Synthesis from D-ribonolactone
83(3)
Bleomycin
86(6)
Synthesis from D-glucosamine
86(1)
Synthesis from L-rhamnose
87(1)
Total synthesis of bleomycin A2
88(4)
Calyculins
92(9)
Synthesis from D-lyxose
92(1)
Synthesis from D-gulonolactone
93(1)
Synthesis from L-idonolactone
94(2)
Synthesis from D-ribonolactone
96(2)
Synthesis from D-erythronolactone
98(3)
Acivicin
101(2)
Bengazole
103(2)
Six-membered nitrogen heterocycles
105(95)
Hydroxymethylpiperidines
105(58)
Nojirimycin
105(2)
Synthesis from D-glucose
107(9)
Synthesis from L-sorbose
116(4)
Synthesis from L-threose
120(1)
Synthesis from D-mannitol
121(1)
Synthesis from gluconolactone
121(1)
Synthesis from glucuronolactone
122(1)
Synthesis from inositols
122(8)
Mannojirimycin
130(1)
Synthesis from D-glucose
130(3)
Synthesis from D-mannose
133(2)
Synthesis from D-fructose
135(1)
Synthesis from D-gluconolactone
135(1)
Synthesis from gulonolactone
136(2)
Synthesis from D-glucuronic acid
138(1)
Synthesis from sucrose
138(3)
Galactonojirimycin (galactostatin)
141(1)
Synthesis from D-galactose
141(3)
Synthesis from D-glucose
144(2)
Synthesis from L-sorbose
146(1)
Synthesis from L-threose
147(2)
Synthesis from D-ribonolactone
149(2)
Fagomine
151(1)
Synthesis from D-glucose
151(1)
Synthesis from D-glucal
152(3)
Homonojirimycin analogues
155(1)
Synthesis from D-galactose
155(2)
Synthesis from D-glucose
157(1)
Synthesis from D-mannose
157(3)
Synthesis from erythrose
160(1)
Synthesis from aldonolactones
160(3)
Miscellaneous substituted piperidines
163(37)
2,6-Disubstituted 3-hydroxypiperidines
163(1)
Synthesis from D-glucose
164(3)
Synthesis from D-glucal
167(3)
Synthesis from D-glyceraldehyde
170(2)
Synthesis from L-gulonolactone
172(1)
Synthesis from calcium D-gluconate
173(4)
Hydroxylated pipecolic acids
177(1)
Synthesis from D-glucose
177(1)
Synthesis from D-glucosamine
178(1)
Synthesis from D-glucuronolactone
178(2)
Synthesis from heptono-1,4-lactone
180(2)
Sesbanimide
182(1)
Synthesis from D-glucose
182(4)
Synthesis from D-xylose
186(1)
Synthesis from D-threose
187(1)
Synthesis from D-mannitol
187(1)
Synthesis from D-sorbitol
188(5)
Siastatin
193(3)
Meroquinene
196(2)
Pyridyl fragment of pyridomycin
198(2)
Seven-membered nitrogen heterocycles
200(12)
Bengamides
200(9)
Synthesis from D-glucose
201(1)
Synthesis from L-glucose
202(1)
Synthesis from L-mannose
203(1)
Synthesis from D-threose
204(1)
Synthesis from (R)-glyceraldehyde
205(1)
Synthesis from D-glucoheptonolactone
206(3)
Liposidomycins
209(3)
Fused nitrogen heterocycles
212(171)
3:5-Fused heterocycles
212(10)
Azinomycins
212(1)
Synthesis from D-fructose
213(1)
Synthesis from D-glucose
213(1)
Synthesis from D-glucosamine
214(1)
Synthesis from D-arabinose
214(8)
4:5-Fused heterocycles
222(17)
β-Lactams
222(1)
Synthesis from D-allose
223(1)
Synthesis from D-galactose
223(1)
Synthesis from D-glucose
224(3)
Synthesis from D-glucosamine
227(2)
Synthesis from D-arabinose
229(1)
Synthesis from D-xylose
230(2)
Synthesis from L-glyceraldehyde
232(1)
Synthesis from D-glyceraldehyde
232(2)
Synthesis from L-ascorbic acid
234(1)
Synthesis from D-ribonolactone
235(4)
5:5-Fused heterocycles
239(67)
Polyhydroxypyrrolizidines
239(5)
Synthesis from D-glucose
244(4)
Synthesis from D-glucosamine
248(2)
Synthesis from D-mannose
250(1)
Synthesis from D-fructose
251(1)
Synthesis from D-arabinose
252(3)
Synthesis from L-xylose
255(1)
Synthesis from erythrose
256(3)
Synthesis from D-mannitol
259(3)
Synthesis from aldonolactone
262(10)
Trehazolin
272(1)
Synthesis from D-glucose
273(4)
Synthesis from D-arabinose
277(1)
Synthesis from D-mannitol
278(1)
Synthesis from myo-inositol
279(3)
Synthesis from D-ribonolactone
282(3)
Allosamidin
285(1)
Synthesis from D-glucose
286(1)
Synthesis from D-glucosamine
287(4)
Total synthesis of allosamidin
291(9)
(+)-Biotin
300(1)
Synthesis from D-glucose
300(1)
Synthesis from D-glucosamine
300(1)
Synthesis from D-mannose
300(1)
Synthesis from D-arabinose
301(2)
Synthesis from D-glucuronolactone
303(3)
5:6-Fused heterocycles
306(64)
Hydroxylated indolizidines
306(1)
Castanospermines
306(13)
(-)-Swainsonine
319(25)
Lentiginosine
344(5)
Slaframine
349(4)
Miscellaneous
353(1)
Kifunensine
353(2)
Nagstatin
355(2)
Calystegines
357(7)
(-)-Mesembrine
364(2)
Streptolidine
366(4)
6:6-Fused heterocycles
370(13)
Hydroxylated quinuclidines
370(1)
Synthesis from D-glucose
370(1)
Synthesis from D-arabinose
371(4)
Biopterins
375(1)
Synthesis from L-rhamnose
375(1)
Synthesis from D-ribose
376(1)
Synthesis from L-xylose
376(3)
Isoquinolines
379(1)
Calycotomine
379(1)
Decumbensines
380(1)
Laudanosine and glaucine
381(2)
Multi-fused heterocycles
383(40)
Indoloquinolizidines
383(12)
Xylopinine
383(2)
Antirhine
385(2)
Allo-yohimbane
387(2)
Ajmalicine
389(1)
Synthesis from D-glucose
389(2)
Synthesis from D-mannose
391(1)
Synthesis from D-erythritol
391(4)
Indolocarbazole alkaloids
395(7)
Synthesis from L-glucal
396(2)
Synthesis from 2-deoxy-D-ribose
398(4)
Phenanthridone alkaloids
402(17)
Synthesis from D-galactose
403(1)
Synthesis from D-glucose
404(3)
Synthesis from L-arabinose
407(3)
Synthesis from D-lyxose
410(1)
Synthesis from D-gulonolactone
411(8)
Ecteinascidins
419(4)
Natural Source (Natural Product) Index 423(6)
Biological Activities Index 429(4)
Index 433

An electronic version of this book is available through VitalSource.

This book is viewable on PC, Mac, iPhone, iPad, iPod Touch, and most smartphones.

By purchasing, you will be able to view this book online, as well as download it, for the chosen number of days.

Digital License

You are licensing a digital product for a set duration. Durations are set forth in the product description, with "Lifetime" typically meaning five (5) years of online access and permanent download to a supported device. All licenses are non-transferable.

More details can be found here.

A downloadable version of this book is available through the eCampus Reader or compatible Adobe readers.

Applications are available on iOS, Android, PC, Mac, and Windows Mobile platforms.

Please view the compatibility matrix prior to purchase.