226079-79-4Relevant academic research and scientific papers
Synthetic studies of the 18-membered antitumor macrolide, tedanolide. 3. Stereocontrolled synthesis of the C1-C12 part via a synthesis of the C1-C7 fragment by a mismatched but efficient sharpless dihydroxylation and its coupling with the C8-C11 fragment
Matsushima, Tomohiro,Mori, Michiko,Zheng, Bao-Zhong,Maeda, Hiroshi,Nakajima, Noriyuki,Uenishi, Jun-Ichi,Yonemitsu, Osamu
, p. 308 - 321 (2007/10/03)
The C1-C12 part (4) of tedanolide (1) was synthesized starting from methyl (R)-3-hydroxy-2-methylpropionate (11a) via a coupling between the C1- C7 aldehyde (6) and the C8-C11 iodoalkene (7a). For a synthesis of 6, a mismatched but highly efficient Sharpless dihydroxylation of the α,β- unsaturated ester (15) with AD-mix-α was successfully applied. Compound 7a was synthesized using hydrozirconation to the alkyne (32).
Synthetic studies of 18-membered antitumor macrolide, tedanolide. 2. Stereoselective synthesis of the C1 - C7 fragment via a mismatched but highly efficient sharpless dihydroxylation
Matsushima, Tomohiro,Mori, Michiko,Nakajima, Noriyuki,Maeda, Hiroshi,Uenishi, Jun-Ichi,Yonemitsu, Osamu
, p. 1335 - 1336 (2007/10/03)
The C1 - C7 fragment (4) of tedanolide (1) was synthesized starting from methyl (R)-3-hydroxy-2-methyl-propionate via a mismatched but highly efficient sharpless dihydroxylation of the C1 - C7 α,β-unsaturated ester (6) with AD-mix-α.
