First total synthesis of (+)-11-hydroxyerythratidine

Synlett

Volumn , Issue 7, 2009, Pages 1041-1046

  Onoda, Toshio ^a   Takikawa, Yosuke ^a   Fujimoto, Takashi ^a   Yasui, Yoshizumi ^a   Suzuki, Keisuke ^a   Matsumoto, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric synthesis; Biphenyls; Erythrinan alkaloids; Natural product; Spirocenter chirality

Indexed keywords

11 HYDROXYERYTHRATIDINE; ACETAL DERIVATIVE; BIPHENYL DERIVATIVE; ERYTHRINA ALKALOID; LEWIS ACID; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 67649401811     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1088157     Document Type: Article

References (46)

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4. Throughout this work, the commonly accepted erythrinan numbering is used. See: Boekelheide, V.; Prelog, V. In Progress in Organic Chemistry, Vol.3; Cook, J. W., Ed.; Butterworths Scientific: London, 1955, Chap. 5; see also ref. 1.
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35. 4, and concentrated in vacuo. The residue was purified by flash column chromatography (hexane-EtOAc, 3:2) to afford spirocycle 13a (3.75 g, 90%) and 13b (261 mg, 6%).
36. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 712628 (for compound 14) and 712629 (for compound 20). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1 EZ, UK [fax:+44 (1223)336033 or e-mail: deposit@ccdc.cam.ac.uk]; http://www.ccdc.cam.ac.uk/ products/csd/deposit/.
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39. Attempted cyclizations of the derivatives possessing hydroxy or protected hydroxy at C(11) resulted in affording tetracyle 21 (Figure 3) with C(10)-C(11) double bond in various yields. (Chemical Equation Presented)
40. Sakaitani, M.; Ohfune, Y. J. Org. Chem. 1990, 55, 870; and references cited therein.
41. α-Orientation of the C(2)hydrogen in 16-18 was deduced as follows:(1) The assumed ketone intermediate, though not detected, was supposed to be prone to enolization at the C(2) carbonyl to be hydrogenated [cf. epimerization of ketone 19 at C(3)];(2) in compounds 16-18, the NOE was not observed between the hydrogens at C(2) and C(14) while observed in compound 3 with 2β-hydrogen (see ref. 26).
42. Acetylation of 20 [Ac2O, DMAP, pyridine] gave the stereoisomer of ketone 19, which obviously shows that the conversion of 19 into 20 was the two-step process including the deacetylation and the epimerization at C(3). Because α-orientation of the C(3) methoxy in 20 was confirmed by X-ray crystal structure analysis, it leads to β-orientation of the C(3) methoxy in compound 19 as well as 16-18.
43. Reimann, E.; Ettmayr, C. Monatsh. Chem. 2004, 135, 959.
44. The 11β-configuration of 18 was confirmed by employing its C(11) epimer 22 (Scheme 10), obtained as the minor isomer by the reduction with NaBH4 (MeOH, r.t.), in which the NOE was observed between the hydrogens at C(8) and C(11). (Chemical Equation Presented)
45. The preference of the hydride attack from the β-face could be ascribed to the steric hindrance to the α-attack by the axial hydrogen at C(4).
46. R = 12.6 min for 3 (15.4 min for ent-3). NOE was observed between the hydrogens at C(2) and C(14) (Figure 4).