Preparation of (2,2-Dimethylhexahydrofuro[2,3-c]pyrrol-6-yl)methanol: A Conformationally Restricted Congener of Nonproteinogenic 3-Hydroxy-4- methylproline

Synthesis

Volumn , Issue 17, 2003, Pages 2643-2646

  Jao, Edwin ^a   Bogen, Stephane ^a   Saksena, Anil K ^a   Girijavallabhan, Viyyoor ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Conformationally rigid; Nonpeptidic; Prolinol

Indexed keywords

ANTIMONY; ETHERS; OXIDATION;

ETHER MOIETY;

AROMATIC COMPOUNDS;

(2,2 DIMETHYLHEXAHYDROFURO[2,3 C]PYRROL 6 YL)METHANOL; 3 HYDROXY 4 METHYLPROLINE; LACTAM DERIVATIVE; METHANOL DERIVATIVE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; CYCLIZATION; DIASTEREOISOMER; EPOXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0347383729     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42426     Document Type: Article

References (19)

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15. The skeleton of the molecule is readily traced by HSQC, NOESY and COSY experiments. The trans nature of the epoxidation was confirmed by J(H2/H3)= ca. 0 Hz. NOE between H-3 and H-6 was detected (Figure 2). (Equation Presented) Figure 2 Structure of compound 9
16. The structure of 5a was confirmed by the presence of H3-H1a, H3-H7a, H4-H7b and a small H3-H2 NOEs (Figure 3). (Equation Presented) Figure 3 Structure of compound 5a
17. The structure of 5b was confirmed by the presence of H3OH-H6, H3OH-H2, H3-H1a, H4-H1a and H6-H1aNOEs (Figure 4). (Equation Presented) Figure 4 Structure of compound 11
18. The structure of 11 was confirmed by the presence of Me9-H3, Me9-H4, Me10-H5b and H2-H5b NOEs (Figure 5). 1190 (Equation Presented) Figure 5 Structure of compound 11
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