3187-53-9Relevant academic research and scientific papers
Syntheses of pterocarpenes and coumestans via regioselective cyclodehydration
Nayak, Maloy,Jung, Youngeun,Kim, Ikyon
, p. 8074 - 8087 (2016/09/09)
A highly efficient synthetic route to pterocarpenes and coumestans is described. BCl3-mediated dehydrative cyclization of 1,3-diaryloxyacetones under mild conditions permitted regioselective ring closure to afford 3-((2-iodoaryloxy)methyl)benzo
6-endo heck cyclization of 3-(2-iodophenoxy)methylbenzofurans: A useful approach to pterocarpenes
Fowler, Katherine J.,Ellis, Jillian L.,Morrow, Gary W.
, p. 1676 - 1682 (2013/05/21)
Mitsunobu coupling of 3-hydroxymethylbenzofurans with o-iodophenols affords 3-(2-iodophenoxy)methylbenzofurans which under go a useful 6-endo Heck cyclization under Jeffery conditions to afford pterocarpene-type heterocycles. The unsubstituted parent pterocarpene thus prepared was readily converted to coumestan via subsequent PCC oxidation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
Oxidative rearrangement of pentaalkoxychalcones with phenyl-iodine(III) bis(trifluoroacetate) (PIFA): Synthesis of (±)-10-bromopterocarpin and (±)-pterocarpin
Miki, Yasuyoshi,Fujita, Rie,Matsushita, Ko-Ichi
, p. 2533 - 2536 (2007/10/03)
The oxidative rearrangement of pentaalkoxychalcones using the hypervalent iodine compound, phenyliodine(III) bis(trifluoroacetate) (PIFA), has been examined. Treatment of 2,2′-bis(benzyloxy)-4′-methoxy-4,5-methylenedioxychalcone with PIFA gives a rearrangement product in low yield, but 2,2′-bis(benzyloxy)-3-bromo-4′-methoxy-4,5-methylenedioxychalcone yields the rearrangement product, which leads to (±)-bromopterocarpin and (±)-pterocarpin.
Total Synthesis of Sophorapterocarpan A, Maackiain, and Anhydropisatin: Application of a 1,3-Michael-Claisen Annulation to Aromatic Synthesis
Ozaki, Yutaka,Mochida, Keiko,Kim, Sang-Won
, p. 1219 - 1224 (2007/10/02)
A new synthetic route to the pterocarpans using a annulation is described. 1,3-Michael-Claisen condensation of α-methylene-γ-butyrolactones with α-sulphur-substituted ketones gives 6-membered rings which have been converted into the pterocarpan framework by aromatization.Sophorapterocarpan A, maackiain, and anhydropisatin have been prepared employing this new aromatic synthesis.
Aromatic Ring Formation by the 1,3-Michael-Claisen Annulation: Total Synthesis of Sophorapterocarpan A, Maackiain, and Anhydropisatin
Ozaki, Yutaka,Mochida, Keiko,Kim, Sang-Won
, p. 374 - 375 (2007/10/02)
The utility of the 1,3-Michael-Claisen annulation sequence in the synthesis of natural products has been demonstrated by the synthesis of sophorapterocarpan A (1), maackiain (2), and anhydropisatin (3).
