25490-91-9Relevant articles and documents
Intramolecular [4+3] cycloadditions. Towards a synthesis of widdrol
Harmata, Michael,Kahraman, Mehmet,Adenu, Gilbert,Barnes, Charles L.
, p. 583 - 618 (2007/10/03)
Certain substituted alkoxyallylic sulfones were alkylated and treated with Lewis acids to produce vinylthionium ions that underwent intramolecular [4+3] cycloaddition reactions with a tethered furan. Manipulation of the cycloadduct led to the synthesis of widdrol. Other attempts to prepare the cycloadducts were made, but none were exceptionally better than the route using vinylthionium ions as intermediates. Interesting aspects of the alkylation chemistry of phenylthio-substituted alkoxyallylic sulfones are detailed as well.
REARRANGEMENT APPROACHES TO CYCLIC SKELETONS. V. FORMAL BRIDGEHEAD SUBSTITUTION OF 1-METHOXYBICYCLONON-6-EN-2-ONES AND ITS APPLICATION TO A TOTAL SYNTHESIS OF (+/-)-WIDDROL
Uyehara, Tadao,Yamada, Jun-Ichi,Furuta, Toshiaki,Kato, Tadahiro,Yamamoto, Yoshinori
, p. 5605 - 5620 (2007/10/02)
The C-1 methoxy group of bicyclonon-6-en-2-ones is replaced by alkyl, alkenyl, and aryl groups or hydrogen with inversion of the absolute configuration via the two-step sequence consists of Grignard reaction or reduction of the carbonyl followed by
Control of Remote Relative Chiralities: A Stereospecific Total Synthesis of dl-Widdrol
Danishefsky, Samuel,Tsuzuki, Kazuo
, p. 6891 - 6893 (2007/10/02)
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