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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Veröffentlicht in:	Tetrahedron letters 2011-04, Vol.52 (16), p.1847-1850
Hauptverfasser:	Isobe, Minoru, Niyomchon, Supaporn, Cheng, Chia-Yi, Hasakunpaisarn, Anuch
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Beschreibung
Zusammenfassung:	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