SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 8, 2008, Pages 1236-1238

Regiospecific synthesis of the C and D rings of viridin

(2) Muller, Kristine M a Keay, Brian A a

a UNIVERSITY OF CALGARY (Canada)

Author keywords

Furano steroids; Furans; Intramolecular Diels Alder reaction; Viridin

Indexed keywords

FURAN DERIVATIVE; NATURAL PRODUCT; VIRIDIN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 44349166217 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072651 Document Type: Article

Times cited : (10)

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- Experimental Procedure for the Preparation of 10: Compound 12 (0.394 g, 1.33 mmol) was dissolved in CH2Cl2 (25 mL) and the solution was cooled to -78°C. Dimethylaluminum chloride (1.50 equiv) was added slowly to the solution, and the mixture was stirred overnight, warming to r.t. The reaction was then placed in an ice-bath and H2O (10 mL) was slowly added to the reaction. The aqueous layer was shaken gently with CHCl3 (3 x 15 mL) to prevent the formation of an emulsion. The organic layers were combined, dried over MgSO4, filtered, and concentrated in vacuo to provide a brown solid. The crude product was purified by flash chromatography (hexanes-EtOAC, 20:1) to provide phenol 10 as a white solid (0.213 g, 0.720 mmol, 54.1, mp 137-139°C IR (KBr, 3113 (OH, 1669 (C=O, 1222 (CO) cm-1. 1H NMR(400 MHz, δ, 1.95 (m, 1 H, 2.14 (m, 1 H, 2.86 (m, 4 H, 3.16 t, J, 8.0 Hz
- 2: 296.0555; found: 296.0541.

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