Synthesis and reactions of two stereoisomeric 4.5.5.5 fenestranes with bridgehead substituents

Weyermann, Philipp; Keese, Reinhart (2011). Synthesis and reactions of two stereoisomeric 4.5.5.5 fenestranes with bridgehead substituents. Tetrahedron, 67(21), pp. 3874-3880. Kidlington, UK: Elsevier Science 10.1016/j.tet.2011.03.086

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The [4.5.5.5]fenestranes 2 and 3 with two different functionalities were prepared in seven steps with overall yields of 5% and 10%, respectively. For introduction of a bridgehead double bond the removal of the tertiary hydroxy group was investigated in the two stereoisomeric hydroxyketones 12 and 15. Whereas the dehydration readily occurred in 12, a ring opening reaction was observed for 15. (C) 2011 Elsevier Ltd. All rights reserved.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Other Institutions > Emeriti, Faculty of Science

UniBE Contributor:

Keese, Reinhart

ISSN:

0040-4020

Publisher:

Elsevier Science

Language:

English

Submitter:

Factscience Import

Date Deposited:

04 Oct 2013 14:27

Last Modified:

05 Dec 2022 14:08

Publisher DOI:

10.1016/j.tet.2011.03.086

Web of Science ID:

000291072200012

URI:

https://boris.unibe.ch/id/eprint/9774 (FactScience: 215554)

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