期刊
ORGANIC LETTERS
卷 10, 期 12, 页码 2477-2479出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol800749w
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资金
- NCI NIH HHS [R01 CA056304, CA 56304, R01 CA056304-13] Funding Source: Medline
An enantioselective synthesis of the Hsp90 inhibitor geldanamycin was achieved in 20 linear steps and 2.0% overall yield from 2-methoxyhydroquinone. The synthesis is highlighted by a regio- and stereoselective hydroboration reaction; a Sc(OTf)(3)/Et(3)SiH-mediated pyran ring-opening reaction; an enantioselective crotylation to simultaneously install the C8-C9 (E)-trisubstituted olefin, the C10 and C11 stereocenters; a chelation-controlled asymmetric metallated acetylide addition; and an intramolecular copper(I)-mediated aryl amidation reaction to close the 19-membered macrolactam.
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