Exercises in Synthetic Organic Chemistry

by Ghiron, Chiara; Thomas, Russell

• ISBN13: 9780198559436
• ISBN10: 0198559437
• Format: Paperback
• Copyright: 1997-05-15
• Publisher: Oxford University Press

Summary

This book is comprised of a series of exercises in synthetic organic chemistry based around recently published syntheses. Each exercise gives a reference to the original work, a synthetic scheme in which either structures or reagents have been omitted, a series of questions on the exercise, and in most cases references to related literature and useful reviews. The exercises are designed to provide challenges for people with a wide range of backgrounds, from undergraduates to academic staff and industrial group leaders, and they enable readers to increase their vocabulary of synthetic transformations. Taking a novel approach, this volume encourages active participation; instead of absorbing standard strategies, readers are asked to propose solutions to set problems. The exercises are ideal for group discussions in organic chemistry.

Table of Contents

List of Abbreviations	xiii
Introduction	1	(2)
Total Synthesis of (-)-Ovatolide	3	(1)
Total Synthesis of RS-15385	4	(1)
Total Synthesis of Islandic Acid I Methyl Ester	5	(1)
Total Synthesis of (+)-Patulolide C	6	(2)
Asymmetric Synthesis of 1-Deoxy-8,8a-di-epi-castanospermine	8	(1)
Synthesis of a Structure Related to Hydantocidin	9	(1)
Total Synthesis of Cryptophycin C	10	(2)
Total Synthesis of (±)-Leuhistin	12	(1)
The Asymmetric Synthesis of Bryostatin Fragments	13	(1)
The Total Synthesis of (-)-Balanol	14	(2)
Approach to the Synthesis of Pseudopterosins	16	(1)
Total Synthesis of Neodolabellenol	17	(1)
Total Synthesis of (-)-Swainsonine	18	(1)
Total Synthesis of Octalactins A and B	19	(1)
Asymmetric Synthesis of the Milbemycin β3 Spiroketal Subunit	20	(2)
Stereoselective Total Synthesis of (+)+-Artemisinin	22	(2)
The Synthesis of (±)-Prosopinine	24	(1)
Synthesis of a Pretested Flurocarbocyclic Nucleoside	25	(1)
Synthesis of Tropane Alkaloid Calystegine A3	26	(2)
The Synthesis of (±)-Oxerine	28	(1)
Synthesis of an Enantiopure C-4 Functionalised 2-Iodocyclohexanone Acetal	29	(1)
Total Synthesis of (-)-Solavetivone	30	(2)
Total Synthesis of (+)-Himbacine	32	(2)
Synthesis of 5-Hydroxytiagabine	34	(1)
An Approach to Zoanthamine Alkaloids	35	(1)
Total Synthesis of 1233A	36	(2)
Synthesis of a Key Intermediate of 1β-Methylcarbapenem Antibiotics	38	(2)
Total Synthesis of the Enantiomer of Hennoxazole A	40	(1)
Total Synthesis of (+)-Duocarmycin A	41	(1)
Studies Towards the Total Synthesis of Rapamycin	42	(2)
Studies Towards the Total Synthesis of Rapamycin	44	(2)
Studies Towards the Total Synthesis of Rapamycin	46	(1)
Synthesis of Isochromanquinones	47	(1)
The Synthesis of (±)-12a-Deoxytetracycline	48	(2)
Synthesis of a D-chiro-Inositol 1-Phosphate	50	(1)
Stereoselective Synthesis of (±)-Aromaticin	51	(1)
Synthesis of 7-Methyoxycyclopropamitosene	52	(1)
Total Synthesis of (+)-γ-Lycorane	53	(1)
Enantioselective Total Synthesis of (-)-7-Deacetoxyalcyonin Acetate	54	(2)
Total Synthesis of (+)-Tetrahydrocerulenin	56	(1)
Total Synthesis of (+)-Longifolene	57	(1)
Studies toward the Total Synthesis of Cerorubenic Acid-III	58	(2)
Total Synthesis of 10-Decarboxyquinocarcin	60	(2)
Total Synthesis of (+)-Pyripyropene A	62	(1)
Total Synthesis of d,l-Isospongiadiol	63	(1)
Total Synthesis of the Stemona Alkaloid (-)-Stenine	64	(1)
Total Synthesis of (-)-Papuamine	65	(1)
Total Synthesis of (+)-Stoechospermol	66	(2)
Synthesis of the Tricarbonyl Subunit C8-C19 of Rapamycin	68	(2)
Synthesis of the AB Ring Moiety of Ciguatoxin	70	(2)
Total Synthesis of (+)-Carbonolide B	72	(2)
Approach Towards the Asteriscanolide Skeleton	74	(1)
Total Synthesis of (+)-Dolabellatrienone	75	(1)
Total Synthesis of Stenine	76	(2)
Synthesis of 3β-Acetoxydrimenin	78	(1)
The Total Synthesis of (+)-Adrenosterone	79	(1)
Total Synthesis of (-)-Suaveoline	80	(2)
Total Synthesis of (+)-7-Deoxypancratistatin	82	(2)
Enantioselective Synthesis of Deoxynojirimycin	84	(1)
Formal Synthesis of (±)-Aphidicolin	85	(1)
Synthetic Efforts Towards Bruceantin	86	(2)
Total Synthesis of (+)-FR900482	88	(2)
Total Synthesis of (3Z)-Dactomelyne	90	(2)
Total Synthesis of (±)-Acerosolide	92	(1)
Synthesis of a Vindorosine Precursor	93	(1)
Synthesis of (-)-PGE, Methyl Ester	94	(2)
Total Synthesis of (-)-Parviflorin	96	(2)
Total Synthesis of (-)-Chlorothricolide	98	(2)
Synthetic Studies on Furanoheliangolides	100	(2)
Total Synthesis of Staurosporine	102	(2)
Total Synthesis of (-)-Cephalotaxine	104	(2)
The Synthesis of Picrotoxinin	106	(1)
Total Synthesis of (+)-Dactylol	107	(1)
Synthesis of (±)-Ceratopicanol	108	(2)
Total Synthesis of (±)-Myrocin C	110	(2)
Synthesis of Staurosporine Aglycon	112	(1)
Synthesis of (20S)-Camptothecin	113	(1)
Synthesis of a Fragment of (+)-Codaphiniphylline	114	(2)
The Total Synthesis of Indanomycin	116	(2)
A Total Synthesis of Taxol	118	(2)
Total Synthesis of (-)-Grayanotoxin II	120	(2)
Enantioselective Total Synthesis of (-)-Strychnine	122