Tandem ene-reaction/intramolecular Sakurai Cyclisation (IMSC): A novel access to polysubstituted tetrahydropyrans and gamma-butyrolactones using a unique allylation strategy

The ene-reaction between a variety of aldehydes and allylsilane 22 generates highly functionalised homoallylic alcohols 23. These adducts undergo a subsequent Intramolecular Sakurai Cyclisation (IMSC), affording in good yields polysubstituted tetrahydropyran derivatives. Furthermore, oxidative desil...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 7; pp. 958 - 972
Main Authors Marko, IE, Dumeunier, R, Leclercq, C, Leroy, B, Plancher, JM, Mekhalfia, A, Bayston, DJ
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
ene-reactions
NATURAL-PRODUCTS
CARBONYL-COMPOUNDS
SPIROKETALS
TRISUBSTITUTED TETRAHYDROPYRANS
STEREOSELECTIVE APPROACH
POLYCAVERNOSIDE-A
ISMS REACTION
gamma-butyrolactones
alpha-methylene-gamma-butyrolactones
tetrahydropyrans
allylations
EFFICIENT
STEREOCONTROLLED SYNTHESIS
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Summary:The ene-reaction between a variety of aldehydes and allylsilane 22 generates highly functionalised homoallylic alcohols 23. These adducts undergo a subsequent Intramolecular Sakurai Cyclisation (IMSC), affording in good yields polysubstituted tetrahydropyran derivatives. Furthermore, oxidative desilylation of 23 provides an efficient, connective access to a range of gamma-butyrolactones and alpha-methylene-gamma-butyrolactones.
ISSN:0039-7881
DOI:10.1055/s-2002-28506