Practical preparation of bicyclo[3.2.0]hept-3-en-6-ones and its utilisation in stereoselective total synthesis of grandisol and lineatin via a versatile intermediate

New and efficient stereoselective total syntheses have been devised for racemic grandisol and lineatin, two important components of pheromonic blends. They are based on the utilisation of 1,4-dimethylbicyclo[3.2.0]hept-3-en-6-one as a pivotal intermediate. This compound, as well as other bicyclo[3.2...

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Bibliographic Details
Published inTetrahedron Vol. 50; no. 10; pp. 3235 - 3250
Main Authors Confalonieri, Giovanni, Marotta, Emanuela, Rama, Franco, Righi, Paolo, Rosini, Goffredo, Serra, Rossella, Venturelli, Francesca
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 07.03.1994
Elsevier
Subjects
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Terpenoids
Pheromone
Tricyclic compound
Oxygen heterocycle
Ketone
Allylic compound
Total synthesis
Primary alcohol
Stereoselectivity
Acetal
Bicyclic compound
Racemate
Monoterpene
Monocyclic compound
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Summary:New and efficient stereoselective total syntheses have been devised for racemic grandisol and lineatin, two important components of pheromonic blends. They are based on the utilisation of 1,4-dimethylbicyclo[3.2.0]hept-3-en-6-one as a pivotal intermediate. This compound, as well as other bicyclo[3.2.0]hept-3-en-6-ones, are now easily available by a practical bicyclization of the corresponding 3-hydroxy-6-alkenoic acids. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)81119-4