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Volumn , Issue 20, 2007, Pages 3155-3159

Application of a samarium(II)-mediated spirocyclisation in an asymmetric approach to the cyclopentanol motif of stolonidiol

(4) Sloan, Lisa A a Baker, Thomas M a Macdonald, Simon J F b Procter, David J a

a UNIVERSITY OF MANCHESTER (United Kingdom)

b GLAXOSMITHKLINE (United Kingdom)

Author keywords

Asymmetric synthesis; Natural products; Radical reactions; Samarium; Spiro compounds

Indexed keywords

CYCLOPENTANOL; CYCLOPENTANONE DERIVATIVE; DITERPENOID; KETONE; NATURAL PRODUCT; SAMARIUM; STOLONIDIOL; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CRYSTAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 37749006663 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-1000821 Document Type: Article

Times cited : (13)

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22
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- Anhydrous MeOH (4.34 mL) was added to a stirred solution of SmI 2 (0.1 M in THF, 9.20 mL, 0.92 mmol, 4 equiv) at 0°C and the solution was stirred for 10 min, 3E)-3, 3S)-6-(Benzyloxy)-3-(1- hydroxy-1-methylethyl)-4-oxohexyl-idene]dihydrofuran-2 (3H)-one (20; 100 mg, 0.23 mmol, 1.0 equiv) in THF (1.5 mL) was added and the resultant solution was stirred at 0°C for 0.5 h before the reaction was quenched by opening to air and the addition of NaCl (sat. solution in H 2O, 5 mL, The aqueous layer was separated and extracted with 60% EtOAc in PE (40-60°C, 4 x 15 mL, The combined organic extracts were dried (MgSO4, and concentrated in vacuo. Purification by column chromatography [eluting with 30% EtOAc in PE (40-60°C, gave (5R,6R,7S)-6-[2-(benzyloxy)ethyl]-6-hydroxy-7-(1-hydroxy-1- methylethyl)-2-oxaspiro[4.4]nonan-1-one 24; 22 mg, 0.06 mmol, 28, as a clear, colourless oil; [α
- 2)

23
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- CCDC 605754 contains the supplementary crystallographic data for this paper (compound 27). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
- CCDC 605754 contains the supplementary crystallographic data for this paper (compound 27). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

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