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

DOI: 10.1248/cpb.47.308

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Chemical and Pharmaceutical Bulletin p. 308 - 321 (1999)

Update date:2022-08-04

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Authors:

Matsushima, Tomohiro

Mori, Michiko

Zheng, Bao-Zhong

Maeda, Hiroshi

Nakajima, Noriyuki

Uenishi, Jun-Ichi

Yonemitsu, Osamu

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Article abstract of DOI:10.1248/cpb.47.308

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).

Full text of DOI:10.1248/cpb.47.308

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