213978-60-0Relevant academic research and scientific papers
Synthetic studies towards phorboxazole A. A convergent synthesis of the C31-C46 polyene oxane-hemiacetal side chain
Pattenden, Gerald,Plowright, Alleyn T.,Tornos, James A.,Ye, Tao
, p. 6099 - 6102 (1998)
A convergent and stereoselective synthesis of the C31-C46 side chain unit in the marine natural product phorboxazole A, which accommodates five asymmetric centres, three carbon-to-carbon double bonds and an oxane- hemiacetal unit, is described.
C(21)-C(40) of tetrafibricin via metal catalysis: Beyond stoichiometric chiral reagents, auxiliaries, and premetalated nucleophiles
Kumpulainen, Esa T. T.,Kang, Byungsoo,Krische, Michael J.
supporting information; scheme or table, p. 2484 - 2487 (2011/07/09)
Chemical equations presented. The C(21)-C(40) fragment of fibrinogen receptor inhibitor tetrafibricin was prepared in 12 steps from propane diol (longest linear sequence). In this approach, 6 C-C bonds are formed via asymmetric iridium catalyzed transfer
Fluorous mixture synthesis of four stereoisomers of the C21-C40 fragment of tetrafibricin
Zhang, Kai,Curran, Dennis P.
supporting information; experimental part, p. 667 - 671 (2010/12/18)
Four stereoisomers of the C21-C40 fragment are synthesized in a single exercise with the aid of fluorous tagging to encode configurations at C37 and C33. After demixing and detagging, the isomers were found to have substantially identical 1H NM
Total synthesis of (+)-phorboxazole A, a potent cytostatic agent from the sponge Phorbas sp.
Pattenden, Gerald,Gonzalez, Miguel A,Little, Paul B,Millan, David S,Plowright, Alleyn T,Tornos, James A,Ye, Tao
, p. 4173 - 4208 (2007/10/03)
A convergent total synthesis of phorboxazole A (1a), from the C(3-19), C(20-27) and C(33-46) fragments 5, 4 and 91, respectively, concentrating on stereocontrolled formation of the bonds at C(2-3), C(19-20) and C(27-28), is described. Although a coupling reaction between a macrolide ketone and the side chain substituted sulfone, at C(27-28) was not successful, a Wadsworth-Emmons olefination involving the oxane methyl ketone 4 and an oxazole produced the oxane 90 which was next coupled to 91 leading to the C(20-46) unit 100. A further coupling of 100 to 71c at C(19-20) then led to 105, ultimately, and the synthesis was completed by a macrocyclisation reaction from 105, at the C(2-3) alkene bond, followed by deprotection of 106.
