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Synthetic studies on altohyrtins (spongistatins): synthesis of the C29–C44 (EF) portion

✍ Scribed by Takeshi Terauchi; Masataka Morita; Kyoko Kimijima; Yasuhiro Nakamura; Gouichirou Hayashi; Taisaku Tanaka; Naoki Kanoh; Masaya Nakata

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
74 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

The C29-C44 portion of altohyrtins (spongistatins) has been prepared from 1,5-pentanediol and D-glucose in a stereoselective manner. The convergent synthesis relied on a coupling reaction of the C29-C37 vinyl bromide and the C38-C44 Weinreb amide, diastereoselective reduction of the C38 ketone, and stereoselective formation of the C33-C37 (E ring) acetal.

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