82659-86-7Relevant academic research and scientific papers
Stereoselective synthesis of ophiocerin B
Akkala, Bhasker,Damera, Krishna
, p. 164 - 170 (2013/09/12)
A stereoselective total synthesis of ophiocerin B is reported by asymmetric synthesis, starting from L-malic acid. Of the three stereogenic centers, the vic-diols C-3, C-4 were obtained by Sharpless asymmetric dihydroxylation. ARKAT-USA, Inc.
Total synthesis of macrosphelide M from diacetone glucose
Sharma, Gangavaram V. M.,Reddy, Post Sai
experimental part, p. 2414 - 2421 (2012/05/20)
The total synthesis of macrosphelide M is described. The key steps include the preparation of the acid and alcohol fragments from diacetone glucose and (S)-malic acid, respectively, followed by Yamaguchi esterification and macrocyclization of the tris-olefin by ring-closing metathesis. Finally, one-pot deprotection of the PMB and TBS groups with TiCl4 results in the target. The C-3/C-4 stereocenters of diacetone glucose are used for the introduction of four stereocenters, whereas the fifth stereocenter is realized from (S)-malic acid. The total synthesis of macrosphelide M was achieved from diacetone glucose and (S)-malic acid. The key steps include Yamaguchi esterification and macrocyclization of the tris-olefin by the second-generation Grubbs catalyst.
Enantioselective total synthesis of aigialomycin D
Lu, Jiangping,Ma, Junying,Xie, Xingang,Chen, Bo,She, Xuegong,Pan, Xinfu
, p. 1066 - 1073 (2007/10/03)
An efficient, convergent approach for the total synthesis of aigialomycin D 1 is described. Key features of the synthetic strategy include (a) a Sharpless asymmetric epoxidation reaction and selective opening of a 2,3-epoxy alcohol to elaborate the two hy
Asymmetric addition of an electrophile to naphthalenes promoted and stereodirected by alcohol
Fujita,Matsushima,Sugimura,Tai,Okuyama
, p. 2946 - 2957 (2007/10/03)
4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) reacts with 1-methoxy-4-methylnaphthalene to give the 1,4-addition product in the presence of methanol; the reaction does not proceed in the absence of the alcohol. Methoxy exchange (with CD3OD) was al
Use of the Mitsunobu reaction in the synthesis of polyamines
Edwards, Michael L.,Stemerick, David M.,McCarthy, James R.
, p. 5579 - 5590 (2007/10/02)
The Mitsunobu reaction has been used in the synthesis of polyamine analogues. The synthesis of the (R,R), (S,S) and meso-isomers of a tetraamine are described. The chemistry was used to synthesize a fluorinated polyamine analog and a hexaamine.
