Synthesis of bicyclo[4.2.0]octan-2-ol, a substructure of solanoeclepin A

A sesterterpenoid solanoeclepin A (1) has a unique structure including a bicyclo[4.2.0]octane substructure, for which a new synthetic methodology is explored particularly to cyclize functionalized cyclobutane rings. An optically active ( R)-carvone and a racemic cyclohexenone were each converted int...

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Bibliographic Details
Published in:Tetrahedron letters 2011-04, Vol.52 (16), p.1847-1850
Main Authors: Isobe, Minoru, Niyomchon, Supaporn, Cheng, Chia-Yi, Hasakunpaisarn, Anuch
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Conjugates
Cyclobutane
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Lithium
Nucleophiles
Optical activity
Organic chemistry
Preparations and properties
Substructures
Synthesis (chemistry)
Terpenoids
Tetrahedrons
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Summary:A sesterterpenoid solanoeclepin A (1) has a unique structure including a bicyclo[4.2.0]octane substructure, for which a new synthetic methodology is explored particularly to cyclize functionalized cyclobutane rings. An optically active ( R)-carvone and a racemic cyclohexenone were each converted into the respective epoxyvinylsulfones, and then subjected to the heteroatom-directed conjugate addition (HADCA) by a lithium acetylide nucleophile. The intermediate carbanions from HADCA were used for the following epoxide opening reaction yielding the four-membered carbocyclic products.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.01.152