500702-41-0Relevant academic research and scientific papers
Formal total synthesis of fostriecin by 1,4-asymmetric induction with an alkyne-cobalt complex
Hayashi, Yujiro,Yamaguchi, Hirofumi,Toyoshima, Maya,Okado, Kotaro,Toyo, Takumi,Shoji, Mitsuru
supporting information; experimental part, p. 10150 - 10159 (2010/11/20)
The synthesis of a protected dephosphofostriecin, and thereby a formal synthesis of fostriecin, has been accomplished. The synthetic challenges were the construction of four stereogenic centers and the conformationally labile cis-cis-trans-triene moiety. Previous total syntheses have employed at least two asymmetric reactions that required the use of an external chiral auxiliary. Although remote stereoinduction in a 1,4-relationship is considered difficult, we have developed a notable 1,4-asymmetric induction that utilizes an alkyne-cobalt complex for the control of C5 stereochemistry by the C8 stereogenic center. The stereochemistry at C11 was established by 1,3-asymmetric induction with a higherorder alkynyl-zinc reagent. Thus, only one asymmetric reaction requiring an external chiral auxiliary was employed in this route. The labile cis-cis-transtriene unit was constructed at a late stage of the synthesis by diastereoselective coupling of a dienyne and an aldehyde unit, followed by reduction.
Enantio- and stereoselective route to the phoslactomycin family of antibiotics: Formal synthesis of (+)-fostriecin and (+)-phoslactomycin B
Sarkar, Shaheen M.,Wanzala, Everlyne N.,Shibahara, Setsuya,Takahashi, Keisuke,Ishihara, Jun,Hatakeyama, Susumi
supporting information; experimental part, p. 5907 - 5909 (2010/01/31)
A general methodology applicable for the synthesis of the phoslactomycin family of antibiotics, potent and selective protein phosphatase inhibitors, has been developed starting from a β-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of 3-(4-me
Total synthesis of (+)-fostriecin and (+)-phoslactomycin B
Shibahara, Setsuya,Fujino, Masataka,Tashiro, Yasumasa,Okamoto, Nanako,Esumi, Tomoyuki,Takahashi, Keisuske,Ishihara, Jun,Hatakeyama, Susumi
experimental part, p. 2935 - 2953 (2010/03/03)
(+)-Fostriecin and (+)-phoslactomycin B, which are potent and selective inhibitors of protein phosphatase, were synthesized by a highly enantio-and stereoselective approach that enabled us to prepare all possible isomers at both the C11 secondary alcohol position and the δ12-double bond. Georg Thieme Verlag Stuttgart.
Formal total synthesis of fostriecin via 1,4-asymmetric induction using cobalt-alkyne complex
Hayashi, Yujiro,Yamaguchi, Hirofumi,Toyoshima, Maya,Okado, Kotaro,Toyo, Takumi,Shoji, Mitsuru
supporting information; experimental part, p. 1405 - 1408 (2009/04/12)
(Chemical Equation Presented) The synthesis of a protected dephosphofostriecin, and thereby a formal synthesis of fostriecin, has been accomplished. Two of the four chiral centers are controlled by an external chiral auxiliary and the other two are synthesized stereoselectively, one by a novel 1,4-asymmetric induction using cobalt-alkyne complex, and the other by 1,3-asymmetric induction.
Versatile enantiocontrolled synthesis of (+)-fostriecin.
Esumi, Tomoyuki,Okamoto, Nanako,Hatakeyama, Susumi
, p. 3042 - 3043 (2007/10/03)
Fostriecin, a potent protein phosphatase inhibitor and antitumor agent, has been enantioselectively synthesized in naturally occurring form via a versatile route, which also allows one to secure all possible stereoisomeres of the C1-C13 fragment including
