Synthesis of chiral $tricyclo[3.2.1.0^2^,^7]$octanes by an efficient 3-exo-trig radical cyclisation $reaction^1$

Srikrishna, Adusumilli and Sharma, Veera Raghava G (1997) Synthesis of chiral $tricyclo[3.2.1.0^2^,^7]$octanes by an efficient 3-exo-trig radical cyclisation $reaction^1$. In: Journal Of The Chemical Society-Perkin Transactions 1 (2). pp. 177-182.

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Abstract

Synthesis of chiral tricyclo[3.2.1.0(2,7)]octanes by efficient and exclusive 3-exo-trig radical cyclisation of either a bicyclo[3.2.1]oct-6-en-2-yl radical or a bicyclo[2.2.2]oct-5-en-2-yl radical is described. Reaction of the methoxy enones 7a-c with boron tribromide at low temperature furnishes the bicyclo[3.2.1]octenyl bromides 9a-c and 10a-c along with varying amounts of 8a-c, whereas the methoxy enone 7d provides the unrearranged bicyclo[2.2.2]octenyl bromide 8d. Treatment of the homoallyl bromides 9a-c and 10a-c and 8d with tributyltin hydride and AIBN generates, exclusively, the tricyclic ketones 15a-d.

Item Type:	Journal Article
Publication:	Journal Of The Chemical Society-Perkin Transactions 1
Publisher:	Royal Society of Chemistry
Additional Information:	Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	06 Feb 2010 11:00
Last Modified:	19 Sep 2010 05:24
URI:	http://eprints.iisc.ac.in/id/eprint/18690

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