Compound 34

(1R,2R)-2-((1S,3R,3aS,6S,6aR,9R,12bR)-11-Methoxy-3a,10,10-trimethyl-8,12,13-trioxo-1,6-bis((trimethylsilyl)oxy)-1,2,3,3a,4,5,6,7,8,9,10,12-dodecahydro-6a,9-epoxy-3,12b-methanobenzo[4,5]cyclohepta[1,2-e]inden-3-yl)cyclopropanecarbaldehyde

From: Total synthesis of solanoeclepin A

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InChIKey HWYDVFPXHMRAEK-PLKWEVPNSA-N

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

To a solution of alcohol 33 (12.3 mg, 19.6 ÎĽmol) in CH2Cl2 (0.39 mL) was added Dess-Martin periodinane (30.6 mg, 72.1 ÎĽmol) at room temperature. After being stirred for 1.5 h, a saturated aqueous NaHCO3 solution and an aqueous Na2S2O3 solution were added. The mixture was separated, and the aqueous layer was extracted with ether. The combined organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude aldehyde was used for the next step without purification.

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