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Synthesis 1991; 1991(4): 245-262
DOI: 10.1055/s-1991-26438
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Prelog-Djerassi Lactonic Acid. A Target for Design and Development of Stereoselective Synthetic Methods

Stephen R. Martin* , Denise E. Guinn
  • *Department of Chemistry and Biochemistry, The University of Texas, Austin TX 78712, USA
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Publication Date:
29 April 2002 (online)

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Stereoselective construction of new carbon-carbon and carbon-heteroatom bonds constitutes one of the major challenges in modern synthetic organic chemistry. Consequently, numerous methods have been designed and developed to address this problem in both the context of relative and absolute stereochemical control. This review of synthetic approaches to Prelog-Djerassi lactone, which covers the period of 1963-1990, provides a useful overview of many of the useful tactics and devices that may be employed for the stereoselective assemblage of functionalized frameworks. 1. Introduction 2. Non-Stereoselective Syntheses 3. Architecture-Based Syntheses 3.1. Monocyclic Precusors 3.2. Bicyclic Precusors 4. Carbohydrate-Based Syntheses 5. Aldol Reactions 6. Additions of Crotyl Organometallic Reagents to Carbonyl Compounds 6.1. Crotylboronates 6.2. Crotylstannanes 6.3. Crotylsilanes 6.4. Crotylchromium Reagents 7. Pericyclic Reactions 7.1. [4 + 2] Cyclocondensations 7.2. Ene Reactions 7.3. [3,3]-Sigmatropic Rearrangements 7.4. [2,3]-Sigmatropic Rearrangements 8. Electrophilic Additions to Alkenes 8.1. Mercuric Ion Induced Cyclizations 8.2. Intramolecular Hydroborations 8.3. Epoxidations 8.4. Allylsilanes 9. Conclusions