Highly Regioselective Diels−Alder Reactions toward Oroidin Alkaloids: Use of a Tosylvinyl Moiety as a Nitrogen Masking Group with Adjustable Electronics
Organic Letters2005Vol. 7(9), pp. 1679–1682
Citations Over TimeTop 10% of 2005 papers
Abstract
[reaction: see text] The use of the p-toluenesulfonyl (Ts) and tosylvinyl (Tsv) groups as nitrogen masking groups imparted high regioselectivity in Diels-Alder reactions directed toward members of the oroidin-derived marine alkaloid family. The electron-withdrawing Tsv group was utilized as an electronically adjustable nitrogen-protecting group as subsequent hydrogenation provided the more electron-rich tosylethyl (Tse) group. This electronic adjustment strategy avoided a protecting group exchange and provided the required electronics for the key chlorination/ring-contraction sequence.
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