115185-92-7Relevant academic research and scientific papers
Convergent total synthesis of (+)-mycalamide A
Kagawa, Natsuko,Ihara, Masataka,Toyota, Masahiro
, p. 6796 - 6805 (2007/10/03)
The details of a convergent total synthesis of (+)-mycalamide A are descri7bed. Yb(OTf)3-TMSCl-catalyzed cross-aldol reaction conditions are used to synthesize the right segment of mycalamide A. In this reaction, an acid-sensitive aldehyde reacts with methyl trimethylsilyl dimethylketene acetal without epimerization to provide the desired aldol adduct. Additionally, a tetrahydropyran ring, which is the left segment of mycalamide A, is prepared using a novel one-pot δ-lactone formation methodology. Both segments are constructed from a common starting material, D-mannitol. These segments are then coupled in the presence of BuLi, and the functional groups are transformed to complete the synthesis of (+)-mycalamide A.
Total synthesis of (+)-mycalamide A
Kagawa, Natsuko,Ihara, Masataka,Toyota, Masahiro
, p. 875 - 878 (2007/10/03)
A convergent total synthesis of (+)-mycalamide A is described. A Yb(OTf)3-TMSCl catalytic system is used to synthesize a trioxadecalin ring system, which contains the right segment of mycalamide A. In addition, a tetrahydropyran ring, which is
Total synthesis of mycalamide A
Sohn, Jeong-Hun,Waizumi, Nobuaki,Zhong, H. Marion,Rawal, Viresh H.
, p. 7290 - 7291 (2007/10/03)
This communication describes a concise and efficient total synthesis of mycalamide A by the convergent coupling of pederic acid unit with the mycalamine unit. The left-half, (+)-7-benzoylpederic acid, was synthesized from (2R,3R)-3-methylpent-4-en-2-ol in
Total synthesis of mycalamide a and 7-epi-mycalamide A
Roush, William R.,Pfeifer, Lance A.
, p. 859 - 862 (2007/10/03)
formula presented The final stages of a total synthesis of mycalamide A are described. A key step is the aldol reaction (mismatched) of imide 4 and aldehyde 5 which provided a ca. 5:4 mixture of aldols 10a and 10b, with incorrect C(7) stereochemistry. Ela
Total synthesis of mycalamide A. Further synthetic study of the right half
Nakata, Tadashi,Fukui, Hideto,Nakagawa, Tadakiyo,Matsukura, Hiroko
, p. 159 - 164 (2007/10/02)
The right half 5 of mycalamide A (1) was synthesized starting from (R)- or (S)-pantolactone via the Sharpless asymmetric dihydroxylation as the key step. The total synthesis of mycalamide A (1) was accomplished by coupling of the right and left halves.
Chemistry of the mycalamides, antiviral and antitumor compounds from a marine sponge. Part 5. Acid-catalysed hydrolysis and acetal exchange, double bond additions and oxidation reactions
Thompson, Andrew M.,Blunt, John W.,Munro, Murray H. G.,Perry, Nigel B.
, p. 1233 - 1242 (2007/10/02)
The acid-catalysed degradations of the potent antitumor and antiviral sponge metabolite mycalamide A and a triacetyl derivative have been examined.Acetal exchange reactions, catalytic hydrogenation, epoxidation and oxidation reactions have also been perfo
Chemistry of the Mycalamides, Antiviral and Antitumour Compounds from a Marine Sponge. Part 4. Reactions of Mycalamide A and Alkyl Derivatives with Basic Nucleophiles
Thompson, Andrew M.,Blunt, John W.,Munro, Murray H. G.,Clark, Bruce M.
, p. 1025 - 1032 (2007/10/02)
The chemistry of the potent antitumour and antiviral marine sponge metabolite, mycalamide A, and some of its alkyl derivatives, was examined by treatment with alkoxide, hydroxide and oxide bases in various solvents and with azide and hydride in dimethyl sulfoxide.The major rearrangement and cleavage products resulting from these reactions were characterized and tested for in vitro P388 anti-leukaemic activity.
Total Synthesis of Mycalamides A and B
Hong, Chan Yong,Kishi, Yoshito
, p. 4242 - 4245 (2007/10/02)
A total synthesis of mycalamides A (1) and B (2) was accomplished in an enantiomerically pure form, establishing unambiguously their absolute configuration.
