Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis

• Sebastian Krüger and
• Tanja Gaich

Beilstein J. Org. Chem. 2014, 10, 163–193, doi:10.3762/bjoc.10.14

• overview of the new mechanistic insights concerning the title reaction is provided as well as a condensed account on the biological relevance of the topic. Heteroatom variants of this rearrangement are covered briefly. Keywords: cycloheptadiene; divinylcyclopropane rearrangement; domino reactions; natural

• expansion [11][12] as a special case of the DVCPR is not part of this review. The related vinylcylopropane–cyclopentene rearrangement has been reviewed elsewhere [13][14]. Review Mechanistic considerations Transition state. Although the cis-divinylcyclopropane rearrangement is in fact a tethered version of

• ). Davies and co-worker [91][92] investigated the formal synthesis of the sequiterpene-hydroquinone derivative frondosin B (99, see Scheme 12) [93] via an enantioselective cyclopropanation of trans-piperylene and subsequent divinylcyclopropane rearrangement, to further demonstrate the versatility of their