Asymmetric synthesis of (3S,4R,7S)-(-)-3-hydroxy-7-methoxy-2,2,4-trimethyl- decanoic acid, a plausible polyketide fragment of halipeptin A

Tetrahedron Asymmetry

Volumn 14, Issue 21, 2003, Pages 3371-3378

  Della Monica, Carmela ^a   Maulucci, Nakia ^a   De Riccardis, Francesco ^a   Izzo, Irene ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2,2 DIMETHYL 3 HYDROXYPROPIONATE; 3 HYDROXY 7 METHOXY 2,2,4 TRIMETHYLDECANOIC ACID; DECANOIC ACID DERIVATIVE; HALIPEPTIN A; OXAZABOROLIDINE DERIVATIVE; POLYKETIDE; PROPIONIC ACID DERIVATIVE; PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; BROWN CROTYLBORATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL PROCEDURES; CHEMICAL REACTION; COMMERCIAL PHENOMENA; COREY BAKCHI SHIBATA; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0142165176     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00622-0     Document Type: Article

References (19)

1. Randazzo, A.; Bifulco, G.; Giannini, C.; Bucci, M.; Debitus, C.; Cirino, G.; Gomez-Paloma, L. J. Am. Chem. Soc. 2001, 123, 10870-10876. Halipeptins also show a promising antitumor activity, being cytotoxic against HCT-116 human colon carcinoma cells in nanomolar range. William Fenical, personal communication.
2. Randazzo, A.; Bifulco, G.; Giannini, C.; Bucci, M.; Debitus, C.; Cirino, G.; Gomez-Paloma, L. J. Am. Chem. Soc. 2001, 123, 10870-10876. Halipeptins also show a promising antitumor activity, being cytotoxic against HCT-116 human colon carcinoma cells in nanomolar range. William Fenical, personal communication.
3. Della Monica C., Randazzo A., Bifulco G., Cimino P., Aquino M., Izzo I., De Riccardis F., Gomez-Paloma L. Tetrahedron Lett. 43:2002;5707-5710.
4. Brown, H. C.; Bhat, K. S.; Randad, R. S. J. Org. Chem. 1989, 54, 1570-1576. This reaction was chosen for its flexibility: it is possible to prepare, in principle, the four C-3 and C-4 stereoisomers reacting the aldehyde 6 with the (E)- and (Z)-enantiomeric crotyl boranes.
5. Herscovici J., Antonakis K. J. Chem. Soc., Chem. Commun. 1980;561-562.
6. The e.e. of compound 7 was evaluated through deacetylation to give 14 (reported later) and transformation of the ester according the reported synthetic sequence (see Section 4), because of the very low reactivity of the C-3 secondary alcohol of 14 toward the MTPA chlorides (Scheme 5).
7. In an attempt to increase the crotylboration's yields we chose the supposed sterically less demanding 3-[(tert-butyl-diphenylsilyl)-oxy]-2,2- dimethyl-propanal 5c (synthesized through the reported reaction sequence). However, also in this case, the yields of the crotylboration step were low (25-35%) (Scheme 6).
8. Urbanek R.A., Sabes S.F., Forsyth C.J. J. Am. Chem. Soc. 120:1998;2523-2533. (ozonolysis of 7 gave also some α,β-unsaturated aldehyde 8a, see experimental part).
9. Amemiya S., Kojima K., Sakai K. Chem. Pharm. Bull. 32:1984;4746-4751.
10. Corey E.J., Marfat A., Hoover D.J. Tetrahedron Lett. 22:1981;1587-1590.
11. Baskaran S., Baig M.H.A., Banerjee S., Baskaran C., Bhanu K., Deshpande S.P., Trivedi G.K. Tetrahedron. 52:1996;6437-6452.
12. Pohnert G., Boland W. Eur. J. Org. Chem. 2000;1821-1826.
13. β-Hydroxy aldehydes appear to be less base-labile than β-acetoxy aldehydes. This seemed evident, for example, considering that the ozonolysis of the omoallyl alcohol 14 gave no elimination byproducts.
14. Blanchette M.A., Choy W., Davis J.T., Essenfeld A.P., Masamune S., Roush W.R., Sakai T. Tetrahedron Lett. 25:1984;2183-2186.
15. (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504;
16. (b) Motoyoshi, H.; Ishigami, K.; Kitahara, T. Tetrahedron 2001, 57, 3899-3908. Substoichiometric amounts of (R)-MeCBS reagent gave lower yields of diastereomeric alcohols; lower temperatures (-40°C) did not increase the d.r.
17. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096. The Δδ values for the protons at C-4 and C-6 were, respectively, -0.05 and -0.13; while for the protons at C-10 it was 0.05, confirming a (R) configuration for the stereogenic centre at C-7 for 20.
18. Kinney W.A., Zhang X., Williams J.I., Johnston S., Michalak R.S., Deshpanade M., Dostal L., Rosazza J.P.N. Org. Lett. 2:2000;2921-2922.
19. Finch N., Fitt J.J., Hsu I.H.S. J. Org. Chem. 40:1975;206-215.