105518-12-5Relevant articles and documents
Carbohydrate-Based Studies Toward the Synthesis of Hamigeromycin E: A Stereoselective Total Synthesis of an Isomer of Zeaenol
Saidachary, Gannerla,China Raju, Bhimapaka
, p. 425 - 435 (2016/07/06)
A stereoselective synthesis of 14-membered macrolide hamigeromycin E (6) has been studied by employing ortho-lithiated formylation, Barbier allylation, Julia–Kocienski olefination, Mitsunobu esterification, and ring-closing metathesis (RCM) reactions. The
Total synthesis of (+,-)fredericamycin A
Saint-Jalmes, L.,Lila, C.,Xu, J. Z.,Moreau, L.,Pfeiffer, B.,et al.
, p. 447 - 449 (2007/10/02)
(+,-)-Fredericamycin A was synthesised by construction of an indanone ketal southern half corresponding to the formation of the spiro system and attachment of the northern part using a two step Hauser reaction.Keywords - total synthesis of fredericamycin
Diels-Alder Approaches to Model Compounds Related to Fredericamycin A
Evans, Jonathan C.,Klix, Russell C.,Bach, Robert D.
, p. 5519 - 5527 (2007/10/02)
A series of model compounds related to the antitumor and antibiotic compound fredericamycin A has been prepared.Spiro-2,5-dione (2) has been prepared and established as a novel spiro dienophile in the Diels-Alder reaction with 1,3-butadiene, Danishefsky's diene, a triacetoxy-substituted o-quinodimethane, and two isobenzofuran intermediates.Thus, the cycloaddition of 3-cyano-4,5,7-trimethoxy-1(3H)-isobenzofuranone (35) and 2 afforded 4,9-dihydroxy-5,6,8-trimethoxyspiroindene-2,1'-indan>-1,3-dione (38) in 62percent yield.This methodology provides a viable synthetic route to the quinone portion of fredericamycin A that contains the seven requisite oxygens.