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ChemInform Abstract: Synthesis of Highly Substituted Bicyclo(3.2.0)heptanones from 3- Homoallylcyclobutenones. A Total Synthesis of (.+-.)-Precapnelladiene.

✍ Scribed by J. M. MACDOUGALL; P. TURNBULL; S. K. VERMA; H. W. MOORE

Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Synthesis of Highly Substituted Bicyclo(3.2.0)heptanones from 3-Homoallylcyclobutenones. A Total Synthesis of (Β±)-Precapnelladiene.

-The stereoselective rearrangement of the title cyclobutenones is obtained by heating in xylene and represents a new and general synthetic method for bicycloheptanones. This route is used as key step in the synthesis of sesquiterpene (XIV), which further includes an oxy-Cope ring expansion of reduction product (VIII). -(MACDOUGALL,

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## Synthesis of 3-Substituted Xylopyranosides from 2,3-Anhydropentosides. -The facile regio-and stereoselective epoxide ring-opening of anhydropentosides (V) provides an attractive pathway to 3-substituted analogues, e.g. (VII), (IX), (XI), and (XIII). -(LUGEMWA, F.

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